Chloroacetic Acid Research Articles

Synthesis and Characterization of New Fused Heterocyclic Compounds Consisting of Benzodiazepine, Quinoxaline, Benzimidazole and Thiazole Rings

In this study, new heterocyclic compounds were synthesized through the cyclization reactions of o-phenylenediamine (1) with various organic reagents. Benzodiazepine derivatives (2-4) were obtained by reaction of (1) with ethylacetoacetate, malonic acid and acetyl acetone.Treatment of compound (1) with chloroacetamide, chloroacetic acid, p-bromophenacyl bromide and oxalic acid dihydrate afforded quinoxaline derivatives (5-8), respectively. Reaction of compound (1) with benzoic acid, piperonal, cyclohexanone and carbon disulfide resulted in the formation of compounds (9-12), respectively. Finally, reaction of compound (12) with chloroacetic acid in the presence of potassium hydroxide produced compound (13).

Synthesis of Some Heterocyclic Compounds Derived from 2-Mercapto Benzoxazole

New series of 2-mecapto benzoxazole derivatives (1-20) incorporated into fused to different nitrogen and suphur containing heterocyclic were prepared from 2-meracpto benzoxazole, when treated with hydrazine hydrate to afford 2-hydrazino benzoxazol (1). Compound (1) converted to a variety of pyridazinone andphthalazinone derivatives (2-4) by reaction with different carboxylic anhydride. Also, reaction of (1) with phenyl isothiocyanate and ethyl chloro acetate afforded 3-phenyl-1,3-thiazolidin-2,4-dione-2-(benzoxazole-2-yl-hydrazone) (6). Azomethines (7-10) were prepared through reaction of (1) with aromatic aldehyde, then (7, 8) converted to thaizolidinone derivatives (11, 12). Treatment of (1) with active methylene compounds afforded derivative (13). Reaction of (1) with CS2 and NaOH gave 1,2,4-triazole derivative (14). Treatment of (1) with p-bromophenancyl bromide afforded another 1,2,4-triazole (15). The reaction of 2-mercapto benzoxazole with chloro acetic acid gave (16) followed by refluxing (16) with ortho-amino aniline giving benzimidazol (17). Moreover, the reaction of 2-mercapto benzoxazole with ethyl chloroacetate afforded (18), and then reaction of (18) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4-triazole derivative (20). All compounds were confirmed by their melting point, FT-IR, UV-Vis spectra and 1H-NMR spectra for some of them.

Synthesis of Some new 2-(4-Aryliminophenoxy)N-Arylacetamide Via p-hydroxy benzaldehyde.

Chloroacetamide derivatives (2a-g) have been prepared through reaction of chloroacetyl chloride(1) (which prepared by the reaction of chloroacetic acid with thionyl chloride) with primary aromatic amines and sulfa compounds to afford compounds (2a-g) which then reacted with p-hydroxy benzaldehyde via Williamson reaction to obtaine the new compounds 2-(4-formyl phenoxy)-N-aryl acetamide (3a-g). Finally , compounds (3a-g) will be use as a good synthon to prepare the Schiff bases represented by compounds 2-(4-aryliminophenoxy)-N-arylacetamide (4a-g). through , reaction with some primary aromatic amine. All the prepared compounds were investigated by the available physical and spectroscopic methods.

Pyridin-1-ium carboxyformate–2-chloroacetic acid (1/1)

The asymmetric unit of the title salt co-crystal, C5H6N+·C2HO4 −·C2H3ClO2, comprises a pyridinium cation, a carboxyformate anion and a 2-chloroacetic acid molecule. In the crystal, the components are connected by hydrogen bonds within a one-dimensional chain in the a-axis direction which incorporates rather short, charge-assisted O—H...O hydrogen bonds; the pyridinium-NH group forms bifurcated N—H...(O,O) hydrogen bonds of different strength.

Simulating synergism or antagonism in binary mixtures with different modeling approaches - A case study focused on the effect of disinfection by-products on algal growth.

This paper aims to test several modeling approaches for predicting toxicity of binary mixtures with potential synergy and antagonism. The approach based on the construction of isoboles was first tested and criticized. In contrast to conventional approaches, and in order to be mathematically consistent with the additivity assumptions, non-linear isoboles have been constructed. This approach was compared with that proposed by Minto et al. (2000), which measures deviations from additivity by considering standardized variables and which considers the entire Hill concentration-response curves. The selected models were tested on a case study related to chlorine-based disinfectant by-products (DBPs), using experimental data describing the effect of five DBPs (monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, bromochloroacetic acid and 1,1-dichloropropan-2-one) on a unicellular green algae Raphidocelis subcapitata. The approach based on the construction of isoboles has shown its limitations. Indeed, in cases where the individual substances involved have different slopes in terms of their Hill concentration-effect relationships, the so-called zone of indetermination can be large. Furthermore, conclusions drawn from isoboles based on EC50s or EC20s may not be consistent. Minto's approach makes it possible to construct interaction indicators that consider the entire Hill concentration-response curve. Response surfaces can be constructed to visualize the areas of concentration of the two substances involved that maximize the interaction effects.

Developmental Toxicity of Disinfection Byproducts in F344 Rats: Effects on Pregnancy Maintenance and Eye Development

ABSTRACTBackgroundEpidemiological studies report associations of drinking water disinfection byproducts (DBPs) with adverse health outcomes, including birth defects. Here, we used a rat model susceptible to pregnancy loss (full‐litter resorption; FLR) and eye malformations (anophthalmia, microphthalmia) to test 11 DBPs, including trihalomethanes, haloacetic acids (HAAs), and nitrogen‐containing DBPs (N‐DBPs).MethodsTimed‐pregnant F344 rats received gavage doses of chloroform, chlorodibromomethane, iodoform, chloroacetic acid, bromoacetic acid, dibromoacetic acid (DBA), diiodoacetic acid (DIA), trichloroacetic acid (TCA), dibromonitromethane, and iodoacetonitrile on gestation days (GD) 6–10. Bromonitromethane and TCA were administered via drinking water on GD 6–11. Litters were examined on postnatal days 1 and 6.ResultsAll trihalomethanes tested caused FLR. The di‐ and tri‐halogenated HAAs, but not the mono‐HAAs, caused eye malformations. N‐DBPs caused neither effect at the dosages tested. TCA by gavage caused both FLR and eye defects, whereas drinking water exposure only caused eye defects. Potency rankings for causing FLR were chloroform ≥ iodoform > chlorodibromomethane and the rankings for causing eye defects were DIA > TCA = DBA.ConclusionWe confirmed that trihalomethanes caused pregnancy loss and that di‐ and tri‐HAAs were teratogenic. The N‐DBPs induced neither effect. Potency rankings were inconsistent with rankings seen in vitro.

Synthesis and Antibacterial Properties of New Quinazoline Analogs Catalyzed by Chloroacetic Acid–Immobilized Nanocobaltferrite

ABSTRACTIn this research, an effective procedure for the one‐pot construction of new quinazoline analogs using chloroacetic acid–immobolized nanocobaltferrite (nano‐CoFe2O4@SiO2@CPTES‐[(Ph₂PCH₂)₂‐CH2CO2H]2+2Cl−) as an efficient novel magnetic nanocatalyst under ultrasound irradiation at 80°C was presented. Chloroacetic acid–immobilized nanocobferrite was characterized by FT‐IR, XRD, FE‐SEM, TEM, EDX, TGA, VSM, and ICP‐mass analyses. Furthermore, the nanocatalyst could be comfortably isolated via magnetic attraction and recycled at least five times without remarkable loss of its catalytic activity. Additionally, in this protocol, quinazoline analogs were screened for their antibacterial activity against Pseudomonas aeruginosa and Staphylococcus aureus. The results showed that quinazolines 4a, 4b, 4c, 4d, and 4g had good antibacterial activity toward Pseudomonas aeruginosa and Staphylococcus aureus.

Development and assessment of Carboxymethylated Galactomannan from Seeds of Caesalpinia pulcherrima as an Efficient Disintegrating Agent for Orally Disintegrating Tablet

Current study's objective was to evaluate the disintegration potential of naturally occurring Caesalpinia pulcherrima seedgalactomannan and to chemically modify it for formulation of orally disintegrating tablet formulation. Galactomannan extracted from the Caesalpinia pulcherrima seeds received chemical modification through carboxymethylation in an effort to enhance its hydrophilic nature of galactomannan which enhances disintegration potency. Carboxymethylated Caesalpinia pulcherrima seed galactomannan synthesized by etherification process by using monochloroacetic acid the titrimetric method was used to measure the extent of substitution. Carboxymethyl modification of galactomannan was analysed by, various methods like Zeta potential measurement, DSC thermogramand FT-IR. Ondansetron ODT were prepared separately using isolated and carboxymethylated Caesalpinia pulcherrima seed galactomannan by incorporating different concentrations such as 2, 4, 6 %. Precompression and post compressional evaluation parameters for formulated batches were compared with two ethical marketed formulations. Modified Caesalpinia pulcherrima seed galactomannan was nearly equivalent to reference formulation in quality testing so this work makes modified galactomannan suitable disintegrating agent in tablet formulation. As a conclusion, it can be said thatcarboxymethylated galactomannan from seeds of Caesalpinia pulcherrima is suitable disintegrating agent for ODTs.

Synthesis of 3-Alkyl-5-(diethylaminomethyl)-1-(1,3-thiazole)pyrazoles

By the reaction of 3-alkyl-5-(diethylaminomethyl) pyrazoles with chloroanhydride of monochloroacetic acid, the pyrazoles with chloromethyl carbonyl substituent have been synthesized. Due to presence of reactive COCH2Cl groups in a molecule, the pyrazoles have been subjected to heterocyclization with thicarbamides (thiobenzamide, thicarbamide and phenylthiocarbamide) in the presence of triethyleamine in a medium of ethanol, as a result of which the previously unknown 3-alkyl-5-diethylaminomethyl-1-(1,3-thiazol)substituted pyrazole derivatives have been obtained.

GC-MS Analysis of the Ayurvedic Oil Balaswagandhadi Tailam

ABSTRACT Background: To evaluate the efficacy of alternative medications such as Ayurveda, Sidha, and Unani, the application of advanced analytical tools is essential. Aim: In this study, the Ayurvedic oil Balaswagandhadi tailam, which is prescribed for treating fever, muscle weakness, bone and joint issues, muscle wasting, arthritic pain, neuralgia, and paralysis. Methods: The presence of active component was analyzed using gas chromatography–mass spectrometry (GC-MS) following a prescribed protocol. Results: The GC-MS study disclosed the presence of several essential bioactive compounds, including trans-2-methyl-4-n-pentylthiane, S, S-dioxide, chloroacetic acid, tetradecyl ester, 1,2-benzenedicarboxylic acid, bis(2-methylpropyl) ester, methyl 12,15-octadecadienoate, 11-octadecenoic acid, methyl ester, cis-10-heptadecenoic acid, tetradecanedioic acid, 15-hydroxypentadecanoic acid, octadecanoic acid, levo-menthoxyacetic acid, β-eudesmol trimethylsilyl ether, 1-heptatriacotanol, vitamin E, campesterol, and γ-sitosterol. Conclusion: The compounds identified are known for their various medicinal properties, potentially contributing to the therapeutic effects of Balaswagandhadi tailam. Further research is warranted to explore these findings.

The GC MS Study of One Ayurvedic Formulation, Navayasa Churnam

ABSTRACT Background: Navayasa Churnam is an Ayurvedic medicine traditionally used to treat anemia, heart diseases, skin disorders, piles, and jaundice. Aim: The present study involves GC-MS analysis of Navayasa Churnam, an Ayurvedic medicine traditionally used to treat anemia, heart diseases, skin disorders, piles, and jaundice. Methods: The Churnam was sourced from a reputable Ayurvedic vendor in Chennai, India, and prepared according to standard protocols. The medicine was then analyzed to identify its bioactive compounds. Results: The GC-MS analysis revealed several key compounds, including Asarone, known for its sedative and antioxidant properties; 17-Octadecynoic acid methyl ester, with potential anti-inflammatory effects; n-Pentadecanol, recognized for its antimicrobial activity; and Chloroacetic acid pentadecyl ester, which may possess antiviral properties. Additional compounds identified include n-Butyl cinnamate, noted for its anti-inflammatory and antioxidant effects; Chloroacetic acid tetradecyl ester, which might offer antimicrobial benefits; and 2-ynyl o-anisate, known for its analgesic properties. Piperine, which enhances the bioavailability of other compounds and has anti-inflammatory effects, was also detected. Other notable compounds are Z-10-Methyl-11-tetradecen-1-ol propionate, Carnosic acid, and Ethyl iso-allocholate. Conclusion: The identification of these compounds supports the traditional therapeutic uses of Navayasa Churnam and underscores the importance of integrating modern analytical techniques with traditional knowledge to validate and enhance herbal remedies.

Extraction of Lignocellulose from Rice Straw and Its Carboxymethylation When Activated by Microwave Radiation.

The paper presents the process of cellulose extraction from rice straw using water-alkaline solution treatment and the subsequent process of carboxymethylation of the obtained product when activated by microwave radiation. After mercerization of rice straw, the obtained product contained 89.2% cellulose and 6.7% lignin. The X-ray diffraction pattern of the obtained lignocellulose shows three diffraction peaks in the region typical for the polymorphic modification of cellulose Iβ (2θ = 15.50(78), 21.70(145), 34.70(52)). The degree of crystallinity was 65%. The product was heat-stable up to 247 °C. The synthesis of carboxymethylcellulose (CMC) based on the obtained product included successive processes of thermostating in alcohol-alkali solution and cellulose esterification reaction using monochloroacetic acid. To activate the carboxymethylation process, microwave radiation was used (350 W for 90 s), which made it possible to reduce the reaction time by more than 100 times. Functional group analysis of the carboxylated lignocellulose from rice straw was carried out using an FTIR spectrometer. In the IR spectra, a band with a maximum of 1742 cm-1 was recorded, corresponding to stretching vibrations of >C(O)OH groups. The degree of polymerization was recorded by mass spectrometry.

Ultrafast complete dechlorination enabled by ferrous oxide/graphene oxide catalytic membranes via nanoconfinement advanced reduction

Chlorinated organic pollutants widely exist in aquatic environments and threaten human health. Catalytic approaches are proposed for their elimination, but sluggish degradation, incomplete dechlorination, and catalyst recovery remain extremely challenging. Here we show efficient dechlorination using ferrous oxide/graphene oxide catalytic membranes with strong nanoconfinement effects. Catalytic membranes are constructed by graphene oxide nanosheets with integrated ultrafine and monodisperse sub-5 nm nanoparticles through simple in-situ growth and filtration assembly. Density function theory simulation reveals that nanoconfinement effects remarkably reduce energy barriers of rate-limiting steps for iron (III)-sulfite complex dissociation to sulfite radicals and dichloroacetic acid degradation to monochloroacetic acid. Combining with nanoconfinement effects of enhancing reactants accessibility to catalysts and increasing catalyst-to-reactant ratios, the membrane achieves ultrafast and complete dechlorination of 180 µg L−1 dichloroacetic acid to chloride, with nearly 100% reduction efficiency within a record-breaking 3.9 ms, accompanied by six to seven orders of magnitude greater first-order rate constant of 51,000 min−1 than current catalysis. Meanwhile, the membranes exhibit quadrupled permeance of 48.6 L m−2 h−1 bar−1 as GO ones, because nanoparticles adjust membrane structure, chemical composition, and interlayer space. Moreover, the membranes show excellent stability over 20 cycles and universality for chlorinated organic pollutants at environmental concentrations.

Improved Hydrothermal Conversion of Pea Pod Biomass for Production of Platform Chemicals with Organic Acid Catalysts

Agro-industries produce over 2 billion tons of agricultural waste annually, including by-products like bagasse, molasses, seeds, stems, leaves, straw, and shells. The use of agro-industrial waste is a way to reduce the impact of industrial processes on the environment. The pea pod is a biomass with a high concentration of cellulose, hemicellulose and some lignin; therefore, it can be used to produce platform chemicals by means of a hydrothermal process. There is limited research on the hydrolysis of pea biomass, but it has been shown to obtain high yields. This study analyzed the effectiveness and selectivity of the hydrothermal process using pea pod biomass with a particle size of 0.5 mm at 180 °C for one hour. A 500 mL reactor was used, with a biomass-to-acid solution ratio of 1:20. The concentration of the acid solution was 0.02 M. The concentrations of sugar, formic acid, levulinic acid, HMF, and furfural produced were measured. Among the catalysts studied, adipic acid catalysis showed the highest yield of 65.16%, with 37.09% of sugar, 16.37% of formic acid, and 11.71% of levulinic acid. On the other hand, the catalysts with chloroacetic acid, butyric acid, anthranilic acid, and phthalic acid were less effective but demonstrated selectivity for sugar production, proving that the liquid phase obtained using the catalyst with those acids can be used as carbon sources for a fermentation process. In general, when comparing the process with or without the use of a catalyst, it is observed that with a catalyst in the reaction, the amount of HMF and furfural produced is reduced and the selectivity with respect to sugar production is increased.

Mechanochemical oxidative complexation of copper(I) chloride with acetic acid, benzoic acid, their chloro derivatives and l-histidine affording anhydrous copper(II) complexes

Mechanochemical oxidative complexation of copper(I) chloride with acetic acid, benzoic acid, their chloro derivatives and l-histidine affording anhydrous copper(II) complexes

The efficacy of cryotherapy compared to the other modalities for the management of palmoplantar warts: a systematic review and network meta-analysis

There are several treatment modalities for Palmoplantar Warts (PPW) introduced, but none have been proven to be significantly effective in all patients. The study aims to assess the efficacy and safety of cryotherapy compared to other modalities for PPW. Searches were conducted in Medline, Embase, Scopus, and CENTRAL databases, along with additional reference and citation tracking from included studies. Randomized Controlled Trials (RCTs) comparing various treatments for PPW were included. Two independent pairs extracted the data from the included studies. Outcomes assessed included cure rates, pain scores, recurrence rates, and adverse events. Network meta-analysis using Netmeta in R software was utilized, with treatments ranked by p-scores. A total of 27 RCTs that enrolled 2,539 participants were deemed eligible. As per p-scores, needling yielded the highest odd for the cure rate (p=1.00), followed by intralesional injection of the Measles, Mumps, and Rubella (MMR) vaccine (p=0.90). For the pain score, 76% topical monochloroacetic acid (p=0.13) showed the lowest mean pain score, while cryotherapy yielded the highest score (p=0.90). Furthermore, cryotherapy showed the highest odds for recurrence rate (p=0.75), followed by intralesional injection of Candida antigen (p=0.61). 0.05% intralesional bleomycin (p=0.93) was the highest agent for adverse events rate, followed by cryotherapy (p=0.61). Needling was the most effective in achieving a cure rate. Cryotherapy has the highest odds for pain score and recurrence rate, while 0.05% intralesional bleomycin has the highest adverse events profile.

Frabrication of carboxymethylchitin nanofibers and fish gelatin hybrid gels with robust gel performance

Frabrication of carboxymethylchitin nanofibers and fish gelatin hybrid gels with robust gel performance

Aromatic Structures Govern the Formation of Chlorinated Byproducts in Dichlorine Radical Reactions.

Radical-induced disinfection byproduct (DBP) formation is drawing attention with increasing applications of advanced oxidation processes (AOPs). Cl2•- represents one of the extensively generated radicals in AOPs, whose behavior in DBP formation remains unknown. In this study, we found that aromatic structures serve as the main DBP precursors in Cl2•- reactions by employing diverse groups of model compounds. At a typical Cl2•- exposure of 1.2 × 10-9 M·s, the sum concentrations of 7 regulated aliphatic DBPs (e.g., trichloromethane, chloroacetic acids) are ∼0.10 to 0.48 μM for aromatic precursors and <0.05 μM for aliphatic ones. The DBP formation mechanisms from Cl2•- reactions involved the formation of chlorinated aromatics, radical-induced oxygen incorporation followed by ring cleavage, and the interactions of Cl2•- with ring-cleavage intermediates. In reacting with DOM, Cl2•- reactions produced much fewer aliphatic DBPs (5% of the total organochlorine vs 40% for chlorination) and chloroacetic acids dominated the aliphatic DBPs (usually trihalomethane for chlorination), which can be well interpreted by the precursors and mechanisms proposed. This work comprehensively reveals the precursors, formation patterns, and mechanisms of DBPs during the less-studied Cl2•- reactions, highlighting the importance of eliminating the aromatic structures of DOM before the AOPs.

Advanced reduction processes initiated by oxidative radicals for trichloroacetic acid degradation: Performance, radical generation, and mechanism

The degradation of haloacetic acids (HAAs) in aqueous environments poses a challenge due to their oxidative resistance. Given that HAAs are highly carcinogenic disinfection byproducts, it is imperative to develop effective degradation methods to reduce their potential health risk. In this study, we found that only 27.2% of 200 μM trichloroacetic acid (TCA) was removed in the UV-activated persulfate (PS) system after 2 h, while complete removal was achieved with the addition of 15 mM formic acid (FA). The main products of TCA degradation were dichloroacetic acid and monochloroacetic acid. Results from free radical quenching experiments and electron paramagnetic resonance spectroscopy analyses indicated that reductive carbon dioxide radical (CO2•-) was the main active species responsible for TCA reduction. Oxidative radicals (i.e., SO4•- and •OH) generated from PS activation reacted with FA to form CO2•-, efficiently degrading TCA. The effects of PS and FA concentrations, solution pH, anions (e.g., Cl-, SO42-, and HCO3-), and small organic molecules (e.g., methanol, ethanol, and acetic acid) on degradation efficiency were examined. Overall, this study proposes a simple and efficient method to improve the degradation efficiency of HAAs in the UV/PS system and provides new insights into the advanced reduction processes used for water treatments.

СИНТЕЗ 2-[(5-АРИЛ-2-ФУРИЛ)МЕТИЛЕН]-5,6-ДИФЕНІЛІМІДАЗО[2,1-b][1,3]ТІАЗОЛ-3-ОНІВ

Condensed five-membered nitrogen- and sulfur-containing heterocycles continues to attract the attention of synthetic chemists with high reactivity and a variety of chemical transformations. Due to a wide range of biological activity azole derivatives are proposed for use in modern medicine and biotechnology. It is known that compounds which contains imidazole fragment are part of a number of drugs such as: naphthizine, dibasole, metronidazole. 5-Arylfuran derivatives also have the broad spectrum of biological activity. Convenient method for preparation of arylfuran compounds is a catalytic arylation of furan derivatives with arenediazonium salts under the conditions of Meerwein reaction. In this work the initial 5-arylfuran-2-carbaldehyde were obtained by furan-2-carbaldehyde arylation in the presence of CuCl2 as a catalyst. These aldehydes can be involved in three-component reaction with derivatives of azoles which were described above. Tandem and domino reactions, as well as multicomponent reactions, are increasingly used in the practice of organic synthesis. Multicomponent reactions make possible to synthesize target compounds with greater efficiency, atom economy and contribute to the introduction of the concept of "green" chemistry. We investigated the interaction of 5-aryl-2-furancarbaldehydes with chloroacetic acid and 4,5-diphenyl-1,3-dihydro-2H-imidazole-2-thione. Experiments have shown that this reaction occurs when the reagents are heated in glacial acetic acid and in the presence of fused sodium acetate. In these conditions, chloroacetic acid is cyclized with 4,5-diphenyl-1,3-dihydro-2H-imidazole-2-thione. Under the same conditions, the active methylene group of the thiazolidinone ring formed reacts with aldehydes. As a result 2-[(5-aryl-2-furyl)methylene]-5,6-diphenylimidazo[2,1-b][1,3]thiazol-3-ones are formed. Thus, a synthetic way is proposed for the construction of hybrid structures in which the imidazo [2,1-b][1,3]thiazole fragment is coupled with arylfuran, which makes them perspective objects for screening for biological activity.