Anhydrous Potassium Carbonate Research Articles

Synthesis and structural elucidation of novel quaternary pyridinium salt and indolizine derivatives as an anti-tubercular agent: In Silico and In Vitro screening

The in vitro anti-mycobacterial activity of a novel series of diversely substituted quaternary pyridinium salts (3a-m) and indolizines (5a-h) were assessed against H37Rv strain of Mycobacterium tuberculosis (M.tb). The series of intermediate 1-(2-oxo-2-phenylethyl)-4-(piperidin-1-yl)pyridin-1-ium bromide, which contains a heterocyclic ring molecule, has been prepared by reacting with 4-(piperidin-1-yl)pyridine and phenacyl bromide at room temperature. The final ethyl 3-benzoyl-7-(piperidin-1-yl)indolizine-1-carboxylate analogues were prepared by using pyridin-1-ium bromide with electron-deficient acetylene, undergoing 1, 3-dipolar cycloaddition at the ambient temperature using anhydrous potassium carbonate and N, N-dimethylformamide as a solvent. All the newly synthesized compounds were characterized by spectroscopic techniques such as 1H and 13C NMR, and HRMS. All the synthesized intermediates and final compounds were evaluated for their anti-tubercular activities against H37Rv (ATCC 27294) strain. All the compounds exhibited anti-tubercular activities in the range of 12.5–50 µM. In vitro screening of all derivatives concluded that among all the screened candidates 3k emerged as an active hit with MIC 12.5 µM, 3l and 3m with MIC 25 µM.

In-silico based Designing of benzo[d]thiazol-2-amine Derivatives as Anal-gesic and Anti-inflammatory Agents.

Benzo[d]thiazoles represent a significant class of heterocyclic com-pounds renowned for their diverse pharmacological activities, including analgesic and anti-inflammatory properties. This molecular scaffold holds substantial interest among medicinal chemists owing to its structural versatility and therapeutic potential. Incorporating the benzo[d]thiazole moiety into drug molecules has been extensively investigated as a strategy to craft novel therapeutics with heightened efficacy and minimized adverse effects. The aim of the present research work was to design, synthesize and characterize the new benzo[d]thiazol-2-amine derivatives as potent analgesic and anti-inflammatory agents. The synthesis of the presented benzo[d]thiazol-2-amine derivatives was performed by condensing-(4-chlorobenzylidene) benzo[d]thiazol-2-amine with a number of substituted phenols in the presence of potassium iodide and anhydrous potassium carbonate in dry acetone. IR spectroscopy, 1HNMR spectroscopy, 13CNMR spectroscopy and Mass spectroscopy methods were used to characterize the structural properties of all 13 newly syn-thesized derivatives. The molecular properties of these newly synthesized derivatives were estimated to study the attributes of drug-like candidates. Benzo[d]thiazol-2-amine derivatives were molecularly docked with selective enzymes COX-1 and COX-2. Analgesic and anti-inflammatory activities of synthesized compounds were evaluated by us-ing albino rats. Findings of the research suggested that compounds G3, G4, G6, G8 and G11 possess higher binding affinity than diclofenac sodium, when docking was performed with enzyme COX-1. Compounds G1, G3, G6, G8andG10 showed lower binding affinity than Indometha-cin when docking was performed with enzyme COX-2.In vitro evaluation of the COX-1 and COX-2 enzyme inhibitory activities was performed for synthesized compounds. Compounds G10 and G11 exhibited significant COX-1 and COX-2 enzyme in-hibitory action with an IC50 value of 5.0 and 10 μM, respectively. Using the hot plate method and the carrageenan-induced rat paw edema model, the synthesized compounds were screened for their biological activities, including analgesic and anti-inflammatory activities. Highest analgesic action was exhibited by derivative G11 and the compound G10 showed the highest anti-inflammatory response. Inhibition of COX may be considered as a mechanism of action of these compounds. It was concluded that synthesized derivatives G10 and G11 exhibited significant analgesic and anti-inflammatory effect; therefore, the said compounds may be subjected to further clinical investigation for establishing these as future compounds for the treatment of pain and inflammation.

Design, Synthesis and In vitro Screening of Novel 2-Mercaptobenzothiazole- Clubbed Phenylacetamides as Potential Antibacterial Agents

Background: The frightening rise of bacterial resistance is occurring worldwide and endangering the efficacy of antibiotics. Hence, the development of novel and potent antibacterial is a need of the day. Objective: In this study, we designed and synthesized compounds C1-C11. These compounds are characterized by their FT-IR, NMR and MS spectral data and examined in vitro for their antibacterial activity. Methods: Compounds C1-C11 were synthesized by reacting 2-mercaptobenzothiazole with appropriate chloroacetamide in the presence of anhydrous potassium carbonate and dry acetone at room temperature. To assess the antibacterial activity, minimum inhibitory and minimum bactericidal concentrations were examined by broth microdilution method against the selected strains of both Gram-positive and Gramnegative bacteria. Time-kill kinetics study was also performed as per CLSI guidelines. Results: Compounds C6 and C7 displayed promising activity against Staphylococcus aureus ATCC 43300 with MICs of 9.43 and 7.73 μM, respectively. These two compounds also displayed promising antibacterial activity against S. aureus 5021 with MIC values of 7.53 and 9.68 μM, respectively. In MBC determination, these two compounds (tested in the concentration range of 7.53 to 262.3 μM) displayed bactericidal activity against methicillin resistant S. aureus ATCC 43300, S. aureus NCIM 5021 and S. aureus NCIM 5022. In time-kill kinetics study, compounds C6 and C7 also exhibited bactericidal activity against S. aureus NCIM 5021 and S. aureus ATCC 43300 after 12 h of exposure. In general, all tested compounds exhibited poor activity against Mycobacterium sp. NCIM 2984 and also against tested Gramnegative bacteria Klebsiella pneumoniae NCIM 2706, Escherichia coli NCIM 2065 and Pseudomonas aeruginosa NCIM 2036. Further, computed ADMET properties of C1-C11 showed a favourable pharmacokinetic profile with zero violation of Lipinski’s rule of five. Conclusion: The result showed that in phenylacetamides C6 and C7 presence of phenyl ring substituted with -CF3 group is responsible for their high antibacterial activity against S. aureus ATCC 43300 (MICs, 9.43 and 7.73 μM, respectively). These two compounds also exhibited bactericidal activity respectively against S. aureus NCIM 5021 in time kill kinetics study.

A Novel Preparation and Purification of Ethyl-β-Cyclodextrins

Ethyl-β-cyclodextrin can be widely used for controlled release of drugs, but its application is greatly limited due to the use of toxic ethylation reagents such as diethyl sulfate, chloroethane, and iodoethane in previous synthesis processes. This article expands the application range of ethyl-β-cyclodextrin by using green ethylation reagent instead of previously toxic ethyl reagents to synthesize ethyl-βcyclodextrin. Ethyl-β-cyclodextrins were studied by reaction with diethyl carbonate and β-cyclodextrin in DMF using anhydrous potassium carbonate as catalyst, During the reaction process, in order to avoid oxidation, the samples were kept in a protective atmosphere of N<sub>2</sub> flow. A new green synthesis process for ethyl-cyclodextrins, using silica gel chromatography to synthesize and purify four substituted 6-O-ethyl-cyclodextrins. Their structures were characterized by IR, MS, <sup>1</sup>H-NMR, and <sup>13</sup>C-NMR. The final product with a yield of 4% was obtained by chromatographic separation using acetonitrile-concd aq NH<sub>3</sub>-H<sub>2</sub>O-EtOAc (6:1:3:1) as the eluent. IR data indicate that the obtained product is the expected product. <sup>13</sup>C-NMR characterization indicates that the substitution position of the product is at position 6, <sup>1</sup>H-NMR, and MS characterization indicate that the degree of substitution of the product is 4. This synthesis method takes full advantage of the spatial selectivity of β-cyclodextrin. The method is green and simple. The target product is synthesized in one step, which is superior to previous reports.

Synthesis of novel phthalazine-based derivatives with potent cytotoxicity against HCT-116 cells through apoptosis and VEGFR2 inhibition.

The parent ethyl 3-(4-benzyl-1-oxophthalazin-2(1H)-yl) propanoate (3) has 25 compounds. Their respective mono, dipeptides and hydrazones derivatives were produced by chemoselective N-alkylation via addition reaction of 4-benzylphthalazin-1(2H)-one (2) with ethyl acrylate and anhydrous potassium carbonate to give ethyl 3-(4-benzyl-1-oxophthalazin-2(1H)-yl) propanoate (3). The ester 3 was hydrazinolyzed to give the corresponding hydrazide 3-(4-benzyl-1-oxophthalazin-2(1H)-yl) propanehydrazide (5), then azide 6 coupled with amino acid ester hydrochloride and/or amines to afford several parent esters 8a-c, then a series of hydrazinolyzed reactions occurred to give corresponding hydrazides 9a-c. The hydrazide 9a was subjected to the azide coupling procedure, which resulted in the formation of various dipeptides. Subsequently, it was condensed with various aldehydes to yield hydrazone derivatives 13a-d. Interestingly, compounds 9c, 12b, and 13c exhibited potent cytotoxicity with IC50 values of 1.58, 0.32 and 0.64 μM compared to sorafenib (IC50 = 2.93 μM). Compound 12b exhibited potent VEGFR2 inhibition by 95.2% with an IC50 value of 17.8 μM compared to sorafenib (94.7% and IC50 of 32.1 μM). For apoptosis activity, 12b-treatment induced apoptosis in HCT-116 cells by 21.7-fold, arresting the cell proliferation at S-phase. Finally, it formed a good binding affinity towards VEGFR2 protein with a binding energy of -10.66 kcal mol-1, and it formed binding interactions with the key interactive amino acids.

In vitro Studies of Antibacterial and Antifungal Activity of Novel Substituted Benzimidazole Derivatives

A series of 2-substituted amino-1-(1H-benzo[d]imidazol-1-yl)ethanone was prepared by reacting with benzimidazole and chloroacetyl chloride by stirring method. The resultant compound was dissolved in ethanol and refluxed with aryl/aralkyl amine in the presence of anhydrous potassium carbonate. The tested compounds were evaluated against bacterial agents such as E. coli, P. aeruginosa, K. pneumonia, S. typhi, and S. aureus, amoxicillin has been used as a control drug, and also screened for antifungal activity against C. albicans and A. niger at 50 and 100 mg/mL level, griseofulvin used as control drug. The structure-activity relationship led to the conclusion compound PS3 showed equipotent potent, PS4 showed moderate, and PS2 showed less moderate activity. The aromatic/aliphatic chain containing compounds PS1 and PS5 showed the least activity against all bacteria. Compound PS3, PS4 and PS1 showed better activity against C. albicans at 100 µg/mL concentration. The tested compounds PS1, PS3, PS2 and PS4 showed good activity at 100 µg/mL concentration. The compound PS3 can serve as a lead molecule for further development as a new class of antimicrobial agent. GRAPHICAL ABSTRACT

Synthesis, Spectroscopic (FT‐IR, FT‐Raman), Electronic Properties and Molecular Docking Studies of 1‐(2, 6‐dibromo‐4‐methyl‐phenoxymethyl)‐benzo[f]chromen‐3‐one

AbstractHerein, 1‐(2,6‐dibromo‐4‐methyl‐phenoxymethyl)‐benzo[f]chromen‐3‐one (DBMPBC) is chosen to be thoroughly investigated in terms of structural, spectroscopic (FT‐IR, FT‐Raman) and molecular electronic properties based on density functional theory (DFT). The title molecule is synthesized by the reaction of 5,6‐benzo‐4‐bromomethylcoumarin with 2,6‐dibromo‐4‐methylphenol in presence of anhydrous potassium carbonate in dry acetone. All the computational studies for the selected structure are carried out at the theoretical level DFT/B3LYP/6‐311++G (d, p). The theoretically determined geometrical parameters from optimized structure and experimental values are compared to each other to confirm the structural properties of the molecule. The vibrational wavenumbers are studied by FT‐IR and FT‐Raman spectral techniques in both experimental and computational methods and compared to each other. The detailed vibrational assignments are assigned through potential energy distribution method by VEDA. The MEP surface analysis is carried out in order to identify the potential sites of electrophilic and nucleophilic attack. The Natural Bond Orbital (NBO) study significantly verified the existence of the intermolecular interactions in the molecule. The stability and reactivity properties of the molecule are estimated in terms of HOMO‐LUMO energies. Molecular docking investigations are carried out to simulate the inhibitory impact of the title molecule against the VEGFR2 (PDB: 2XIR) and PI3K (PDB: 2RDO) receptors for anti‐angiogenic therapy in the treatment of NSCLC. ADMET parameters and toxicity properties of the title molecule is conducted.

Synthesis, spectroscopic (FT-IR, FT-Raman), solvent effects (absorption, fluorescence), electronic and biological evaluation of 7-methyl-4-(4-methyl-2-nitro-phenoxymethyl)-2H-chromen-2-one

In this work, the 7-methyl-4-(4-methyl-2-nitro-phenoxymethyl)-2H-chromen-2-one (7MMNPC) is synthesized by the reaction of 7-methyl-4-bromomethylcoumarin with 4-methyl-2-nitro-phenol in presence of anhydrous potassium carbonate using dry acetone as solvent. Then, it is characterized by several spectral and photophysical properties. Most of the analyses have been investigated by experimental and theoretical methods. Initially, molecular structural characteristics have been obtained by optimized structure with DFT/B3LYP/ 6–311++G (d, p) basis set and compared with reported experimental data. The fundamental vibrational modes of the molecule are fully assigned and examined by observed FT-IR and FT-Raman data and compared with harmonic vibrational wavenumbers obtained by the DFT method. The photophysical properties analyses have been conducted to measure the dipole moments in the ground (μg) and excited (μe) state. The Frontier Molecular Orbital (FMO) analysis depicts that energy gap of HOMO- LUMO is 4.04 eV. Molecular Electrostatic Potential (MEP) analyses are carried out to investigate the molecule's electronic properties. The ADMET and pharmacokinetic parameters are calculated to determine whether the synthesized compound has the potential to be a drug. The toxicological properties of the compound have been investigated. The molecular docking study is conducted to determine the molecule's good degree of inhibition against non-small cell lung cancer (NSCLC).

Design, synthesis, and cytotoxic activity of some novel N-(substituted) benzamide derivatives bearing coumarin and 1-azocoumarin compounds

ABSTRACT. Among oxygen-containing heterocyclic compounds such as coumarin and azacoumarin derivatives, the scaffold has become an important construction motif for developing new drugs. Coumarin and its derivatives possess many types of biological activities and have been reported to show significant cytotoxic activity. N-(6,8-disubstituted coumarin-3-yl)benzamides (8a-c) namely (3-N-(benzoyl) aminocoumarin-6-ylmethyl acetate (8a); N-[6-(1-acetylpyrazol-3-yldiazineyl) coumarin-3-yl] benzamide (8b); N-(8-methoxy-6-bromo-coumarin-3-yl) benzamide (8c), were synthesized via a cyclocondensation reaction of 5-(chloromethyl)-2-hydroxybenzaldehyde (3), 5-(pyrazol-3-yl-diazineyl)-2-hydroxybenzaldehyde (4), and 5-bromo-3-methoxy- 2-hydroxybenzaldehyde (5) with N-benzoylglycine (7), in good yield. Treatment of compound 8c with ammonia in the presence of anhydrous potassium carbonate to yield N-(5-bromo-8-methoxy-1-azocoumarin-3-yl) benzamide (9). Compound (9) was acetylated with acetic anhydride to give N-(2-acetoxy-5-bromo-8-methoxyquinolin-3-yl) benzamide (10). N-(substituted coumarin and azacoumarin-3-yl) benzamides (8-10) were tested for their in vitro cytotoxic activity against (HepG2) cell line. Furthermore, DNA flow cytometry investigation over HepG2 cells indicated that compound 8a demonstrated arrest at G1/S stages of the cell cycle and induction of apoptosis by rising pre-G1 stage. Compound 8a displayed a significant tubulin polymerization inhibition.
 
 KEY WORDS: Synthesis, Coumarin, Azacoumarin, Drugs, Cytotoxicity
 Bull. Chem. Soc. Ethiop. 2023, 37(4), 1003-1019. 
 DOI: https://dx.doi.org/10.4314/bcse.v37i4.16

Synthesis and Analgesic Activity of 3-(3-methoxyphenyl)-2-methylsulfanyl-3Hquinazolin-4-one (4) and 3-(3-methoxyphenyl)-2-thioxo-2,3-dihydro1H-quinazolin-4-one (3) Via N-(3- methoxyphenyl)-methyl dithiocarbamic acid (2).

Introduction: 4(3H)-quinazolinone rings have been reported to possess different biological activities such as antibacterial, antifungal, antitubercular, antiviral, anticancer. These activities also include antihypertensive, diuretic, antimicrobial, pesticidal, anticonvulsant, anaesthetic and sedative activities, anti-malarial, and anti-diabetic. Methods/Experimental: The compound, 3-(3-methoxyphenyl)-2-thioxo-2,3-dihydro1H-quinazolin-4-one (3) was synthesized by dissolving Methyl anthranilate and N-(3- methoxyphenyl)-methyl dithiocarbamic acid in ethanol and anhydrous potassium carbonate and refluxed for 23 h and re-precipitated by treating with dilute hydrochloric. When tested for their in vitro analgesic activity using acetic acid induced induced writhing in mice, the compounds had Analgesic activity. Result: The compounds exhibited significant analgesic activity in the range of 74.67 - 83.80% in comparison to control. Conclusions: From our findings, the compounds synthesized have higher analgesic activities as compared to the standard analgesic drug.

Synthesis, characterization and biological study of some new substituted pyrazolo[3,4-d] thiazolo[3,2-a] pyrimidine derivatives

Fused pyrimidines play an imperative role in our life due to their biological importance in the struggle of microorganisms. A series of 4-aryl-3-methyl-1-phenyl-1,4,6,7-tetrahydropyrazolo[3,4-d] thiazolo[3,2-a]pyrimidine (4a-j) were synthesized by cyclization of 3-methyl-1-phenyl-4-aryl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-d]pyrimidine-6-thiones (3a-j) with 1,2-dibromoethane in presence of anhydrous potassium carbonate. Earlier, compounds (3a-j) were synthesized by the condensation of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2), different substituted benzaldehyde and thiourea with catalytic amount of con. HCl in methanol. Compound 2 was synthesized by condensation of ethyl acetoacetate (1) and phenylhydrezine in presence of a catalytic amount of acetic acid at reflux temperature. The constitution of the synthesized products has been characterized by using elemental analysis, Infrared, 1H-NMR spectroscopy and further supported by Mass spectroscopy. All the products have been screened for their in-vitro biological assay like antibacterial and antifungal activity at concentration of 500 μg/ml. It was exposed that most of the compounds displayed inspiring antibacterial and antifungal activity compared to the used reference standard.

Synthesis, Computational Study, and Anticonvulsant Activity of Newly Synthesized 2-aminobenzothiazole Derivatives

Background:Despite the fact that anticonvulsant drugs targeting multiple targets have been used in the health center, their effectiveness and tolerability in the treatment of seizures have not improved much. As a result, innovative anticonvulsant medicines are still needed urgently to overcome the significant toxicity of currently existing medications.Objective:This study aimed to synthesize 2-aminobenzothiazole derivatives as anticonvulsant agents, compute physicochemical parameters, and conduct a docking investigation.Methods:Condensing 4-(2-(benzo[d]thiazole-2-ylamino) acetamido) benzoyl chloride with substituted phenols in acetone in anhydrous potassium carbonate in the presence of potassium iodide in dry acetone yielded benzothiazole derivatives. IR and NMR spectroscopy were used to characterize the structures of freshly synthesized substances. To estimate their drug-like candidates, a number of molecular attributes of these derivatives were computed. The carbonic anhydrase enzyme was used to perform molecular docking on these synthesized compounds. The synthetic compounds were tested for biological activity, such as anticonvulsant activity and enzyme inhibitor activity for carbonic anhydrase.Results:The findings showed that V-5 (4-chlorophenyl 4-(2-(benzo[d]thiazol-2-ylamino)acetamido)benzoate) had the strongest anticonvulsant effect out of all the eight target compounds.Conclusion:The outcome of this research was that V-5 could be a promising new lead molecule for the development of anticonvulsant drugs.

Synthesis and Antimicrobial activity of 1-(3-amino-5-chloro-2, 3-dihydro-1-benzofuran-2-yl) ethan-1-one [2, 1-b]-furan and their derivatives

The current study is focused on the conversion of 2- chlorosalicylaldehyde into its oxime which was then converted into 5-chloro-2-hydroxy-benzonitrile 1, a key starting material for the present synthetic work. The nitrile 1 on reaction with chloroacetone/phenacyl bromide/4-chlorophenacyl bromide in anhydrous acetone and potassium carbonate gave 2-acyl-3- amino-5-chlorobenzofuran (2a-c). Acetylation of compounds 2a-c furnishes 2-acyl-3acetamido-5- chlorobenzofuran (3a-c). Compounds 3a-c on further treatment with hydrazine hydrate undergo ring closure producing 3-amino-8- chloro-2, 4-dimethyl-3, 4-dihydro [1] benzofuran [3, 2- d] pyrimidin-4-ol (4a-c). The synthesised compounds were characterised by spectral and analytical data and screened for antibacterial and antifungal activity.

Synthesis and Antibacterial Activity of 3-(3-methoxyphenyl)-2-methylsulfanyl-3Hquinazolin-4-one (4) and 3-(3-methoxyphenyl)-2-thioxo-2,3-dihydro1H-quinazolin-4-one (3) Via N-(3- methoxyphenyl)-methyl dithiocarbamic acid (2)

Introduction: Heterocyclic compounds have already provided a platform for the rapid swap of research in the areas of organic, pharmaceutical, analytical, and medicinal chemistry. In the pharmaceutical industry, among the top two hundred branded drugs, more than 75% have heterocyclic fragments in their structures. Methods/Experimental: The compound, 3-(3-methoxyphenyl)-2-thioxo-2,3-dihydro1H-quinazolin-4-one (3) was synthesized by dissolving Methyl anthranilate and N-(3- methoxyphenyl)-methyl dithiocarbamic acid in ethanol and anhydrous potassium carbonate and refluxed for 23 h and re-precipitated by treating with dilute hydrochloric. The 3-(3-methoxyphenyl)-2-thioxo-2,3-dihydro-1Hquinazolin-4-one was dissolved in 40 mL of 2% alcoholic sodium hydroxide solution and dimethyl sulphate was added drop wise with stirring for 1 h, the reaction mixture was then poured into ice water to get 3-(3-methoxyphenyl)-2-methylsulfanyl-3Hquinazolin-4-one (4). The synthesized compounds were screened against various strains of microorganism; Staphylococcus aureus, Bacillus species, Escherichia coli, Klebsiella pneumonia, Enterococcus Feacalis, Pseudomonas aeriginosa, and candida albicans. Compounds 3 and 4 showed significant activity against Staphylococcus aureus, Bacillus species, Escherichia coli, Klebsiella pneumonia, Enterococcus Feacalis, Pseudomonas aeriginosa, and candida albicans, MIC ranging from 6 – 12 mg/mL. Result: The compounds exhibited significant antibacterial activity in comparison to control. Conclusions: From our findings, the compounds synthesized have higher antibacterial activities as compared to the standard antibacterial drug.

Synthesis, Biological Activities and Molecular Docking analysis of a Novel Series of 11H-Indeno[1,2-b]quinoxalin-11-one Derivatives

In this study, olefin adducts were synthesized from Wittig reactions on carbonyl group and stereo-identity of the alkene products. The reaction of 11H-Indeno[1,2-b]quinoxalin-11-one with few stabilized phosphonium ylides yielded a combination of the corresponding E and Z olefins in each case. On the other hand, the reaction of 11H-indeno[1,2-b]quinoxalin-11-one with dialkyl phosphites gave related phosphonates. The aldol condensation reaction of 11H-Indeno[1,2-b]quinoxalin-11-one with boiling dry acetone and/or 2-butanone in presence of aluminum oxide or anhydrous potassium carbonate as a catalyst led to the formation of the β-hydroxy ketones. The nucleophilic addition reaction of acetone and/or 2- butanone to (E)-alkyl 2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)acetate in presence of aluminum oxide or anhydrous potassium carbonate as a catalyst led to the formation of the corresponding an addition products.Reaction mechanisms are taken into consideration and the structural assignments of the new compounds are based on the chemical and spectroscopic evidences. The cytotoxic activity of some new compounds had been evaluated against human hepatocellular carcinoma cell line (HePG2) and human Caucasian breast adenocarcinoma (MCF7). Compounds 6b,c showed higher cytotoxicity towards breast (MCF7) most cancers cellular line than the reference drug (Doxorubicin). The binding mode of phosphonates 6 changed into similarly tested by using molecular docking studies

Vibratile Dihydrophenazines with Controllable Luminescence Enabled by Precise Regulation of π-Conjugated Wings

Vibratile Dihydrophenazines with Controllable Luminescence Enabled by Precise Regulation of π-Conjugated Wings

Synthesis and Antimicrobial Evaluation of Quinazoline-4[3H]-one Derivatives

The present investigation aimed to synthesize quinazoline-4(3H)-one derivatives (B1-10) and evaluated their antimicrobial activity. The test compounds (B1-10) were obtained by reaction of 2- phenyl-4H-benzo[d] [1, 3]oxazin-4-one (1) with 4-aminophenol (2) to afford 3-(4-hydroxyphenyl)-2- phenylquinazoline-4(3H)-one (3) which were further reacted with different N-phenylacetamide (4) in the presence of anhydrous potassium carbonate and a catalytic amount of potassium iodide in ethylmethylketone. The test compounds (B1-10) were characterized by the spectroscopic method and evaluated for their antimicrobial activity using the cup plate method by measuring the zone of inhibition. Among the compounds, compound B1, B2, B4, B6, and B8 showed maximum zone of inhibition as compared to standard drug ciprofloxacin and fluconazole against Bacillus subtilis, Escherichia coli and Aspergillus niger. Molecular docking was also performed for test compounds to predict their binding affinities in the target protein and results showed good drug-like properties.

Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity

This research aimed to produce new 1-[(aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic acid derivatives and check their anticancer effect against the breast cancer MCF-7 cell line. The 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (4) compound was obtained by hydrolyzing ethyl 2-oxo-1,2-dihydroquinoline-3-carboxylate (2) with thiourea and anhydrous potassium carbonate ethanol, which was then treated with ethyl 3-substituted 2-cyanoacrylates (6) in the presence of triethylamine in diethyl formamide to give 1-[2-(ethoxy)carbonyl-2-cyano-1-arylvinyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic (7a,d). Cyclization of compound 7 with hydrazine hydrate ethanol inferred the association of 1-[(aryl)(3 amino-5-oxopyrazolidin-4-ylidene)methyl-2-oxo-1,2-dihydroquinol-3-carboxylates (8a,d). Spectroscopic and micro-analytical techniques such as IR, NMR, and elemental analysis were used to validate the structure of the synthesized organic compounds. The anticancer effects of the synthesized compounds 7a–d and 8a–d were tested by using the MTT assay on the MCF-7 cell line. When compared to the reference compound Dox, the compounds 7b,c and 8a–c demonstrated strong anticancer activity against the MCF-7 cell line. The anticancer effects of the synthesized compounds 7a–d and 8a–d were tested against the MCF-7 cell line, using MTT assay. The compounds 7b,c and 8a–c showed significant anticancer activity compared to the reference compound Dox against the MCF-7 cell line.

Synthesis and Characterization of Some New Coumarin Derivatives as Probable Breast Anticancer MCF-7 Drugs

This study aimed to synthesize quinolinone derivatives and investigate their cytotoxic activity. The compound 1-azacoumarin-3-carboxylic acid (2-oxo-1H-quinoline-3-carboxylic acid) was obtained via the cyclocondensation of 2-hydroxybenzaldehyde with diethyl malonate in base catalyst to give ethyl coumarin-3-carboxylate, followed by the ammonolysis of ester (ethyl coumarin-3-carboxylate) with ammonia in the presence of anhydrous potassium carbonate. Treatment of 2-oxo-1H-quinoline-3-carboxylic acid with acetic anhydride, cinnamaldehyde, cinnamic acid and methyl 5-phenyl-2-cyano-2,4-pentadienoate under different conditions led to the formation of 1 (substituted) aza coumarin-3-carboxylic acids (1-N-(acetyl)-azacoumarin-3-carboxylic acid, 1-N-(2-Formyl-1-phenyl) vinyl-azacoumarin-3-carboxylic acids, 1-N-[2-(Hydroxy) carbonyl-1-(Phenyl) vinyl]-azacoumarin-3-carboxylic acid and 1-N-(4-Cyano-5-methoxy-5-oxo-1-Phenylpenta-1,3-diene-1-y)-azacoumarin-3-carboxylic 284 acid), respectively. The structures of synthesized 1-(substituted) azacoumarin-3-carboxylic acids were confirmed based on spectroscopic methods (IR and NMR), along with elemental analyses. Interestingly compound 6 demonstrated probable impacts as an anti-cancer drug against the MCF-7 cell line. The mechanism of action was assessed using a flow cytometric assay. The outcomes revealed that compound 6 could arrest the cell cycle at G2/M phase and pre-G1 apoptosis.

CONSISE SYNTHESIS AND POTENTIAL ANTI-ANGIOGENIC ACTIVITY OF N-1 SUBSTITUTED INDOLYLCHALCONE HYBRIDS ON CHORIOALLANTOIC MEMBRANE (CAM) ASSAY

Objective: Synthesis of N-1 Substituted Indolylchalcone Hybrids and evaluation of anti-angiogenic activity using Chorioallantoic Membrane (CAM) Assay.
 Methods: Claisen-schmidt reaction is used for the synthesis of 30 Indolylchalcone hybrids, it involves condensation of N-1 substituted indole-3-carboxaldehyde and N1 substituted 2-acetyl-benzimidazole. The phase transfer catalyst, a green catalyst such as anhydrous potassium carbonate (K2CO3) and PEG-400 are used in the alkylation and arylation. All synthesized indolylchalcone hybrids were evaluated for their antiangiogenic activity by in vivo-chorioallantoic membrane (CAM) assay method.
 Results: The synthesized indolylchalcone compounds are evaluated. The morphometric study was carried out as described by Melkonian et al. (2002). The Compounds with code C-2, I-1, I-2 are showing the more potent effect on the dose-dependent assay of CAM. The compounds with code C-1, C-3, E-1 to E-3, M-1 and M-5 shows the significant activity, however, though the compounds with code B-1, B-2, CL-1 and A-5 were showing antiangiogenic effect at 0.1 µM, but does not show any significant activity on dose-dependent assay of CAM.
 Conclusion: The synthesized Indolylchalcones as shown in the graph possess very good dose-dependent anti-angiogenic activities. The potency of anti-angiogenetic activity shows that methyl>Ethyl>Cl-benzyl>Benzyl>Isobutyl. 2-acetyl benzimidazole analogs have possible future scope to develop as potent angiogenesis inhibitors.