Synthesis Of Novel Thiazoles Research Articles

Synthesis of Novel Thiazoles Based on (+)-Usnic Acid

Synthesis of Novel Thiazoles Based on (+)-Usnic Acid

Synthesis of novel thiazoles bearing lupeol derivatives as potent anticancer and anti-inflammatory agents

Lupeol is one of the most important metabolite in the class of terpenoids and possess excellent anticancer, anti-inflammatory, anti-diabetic activities etc. In the present study, the different thiazoles and oxazoles bearing lupeol derivatives were prepared to enhance their biological activity. Initially, the in vitro cytotoxic activity results showed that the synthesized lupeol derivatives (9a–9j and 10a–10e) showed significant activity against various cancer cells and the compounds 9h and 10b exhibited excellent activity against CAL27 cells. Further, these compounds 9h and 10b arrest the cell cycle at S phase and induce the late apoptosis in CAL27 cells by downregulating the BcL2 and vimentin expression and upregulating the Bax gene expression. Moreover, the lupeol derivatives showed dose-dependent anti-inflammatory activity by inhibiting the secretion of IL-6 cytokines in LPS-induced Raw 264.7 cells. Together, these results clearly indicated that the thiazoles and oxazoles bearing lupeol derivatives can used as chemotherapeutic drugs against cancer and inflammatory diseases.

Thiazoles: A Retrospective Study on Synthesis, Structure-activity Relationship and Therapeutic Significance

Abstract: Thiazole or 1,3-thiazole is a distinct heterocyclic compound which incorporates sulphur and nitrogen atoms. It is a vital framework present in numerous pharmacologically active compounds, be it of natural origin or of synthetic nature. Many thiazoles having antitumor and antiviral activities, originate from microbes and marine organisms. A variety of synthetic drugs, having thiazole group, like antimicrobial sulfathiazole, antibiotic penicillin, antidepressant pramipexole, antineoplastic agent bleomycin, antiretroviral drug ritonavir, histamine H2 receptor antagonist nizatidine, anti-inflammatory drug meloxicam, antifungal stilbene derivatives have been in the markets for quite some time. Hofmann and Hantzsch laid the groundwork for further development in the field of thiazole chemistry. The interaction of α-haloketones or α-halogenaldehyde and thioamide to obtain thiazoles is beautifully described by Hantzsch. Various studies have reported methods for the synthesis of the thiazoles; thioforamide, thiourea, α-thiocyanotoketones, and vinyl bromide have been extensively employed to synthesize thiazoles. The thiazoles have immense potential and this study tries to enlighten the crucial role of thiazoles for the betterment of society. The review provides different directions in the synthesis of novel thiazoles and also reveals diverse targets for augmentation in the field of designing of novel thiazoles. Keywords: Thiazoles, Synthesis, QSAR, Molecular Docking, Biological Activity

New Convenient Routes of Hydrazonoyl Halides for the Synthesis of Novel Thiazoles and Polythiazoles

The present effort is to use good organized method for the synthesis of novel thiazoles from the reaction of different α-haloketohydrazonoyl halides with thiosemicarbazones in the basic medium at refux. In addition, new polthiazole was prepared from the reaction of 1,4-phenylene-bis(2-oxopropanehydrazonoyl chloride) with 2,2′-(1,4-phenylenebis(methanyl-ylidene))bis(hydrazine-1-carbothioamide) in the presence of basic medium. The formation of the final thiazoles or polythiazole can be explained through nucleophile substitution of the halogen atom form hydrazonoyl halides, followed by removal of water to give the final products as represented in Schemes. The inexpensive, good yielding, simple reaction conditions, and commercial availability of the chemicals make these methods valuable. The description structures for the final compounds are discussed and suggested. New organic substances were elucidated via FTIR, MS, NMR, and elemental analyses.

One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents.

BackgroundThiazole and thiosemicarbazone derivatives are known to have potential anticancer activity with a mechanism of action related to inhibition of matrix metallo-proteinases, kinases and anti-apoptotic BCL2 family proteins.Materials and MethodsA novel three series of 5-(1-(2-(thiazol-2-yl)hydrazono)ethyl)thiazole derivatives were prepared in a one-pot three-component reaction using 2-(2-benzylidene hydrazinyl)-4-methylthiazole as a starting precursor. MS, IR, 1H-NMR and 13C-NMR were used to elucidate the structures of the synthesized compounds. Most of the synthesized products were evaluated for their in vitro anticancer screening against HCT-116, HT-29 and HepG2 using the MTT colorimetric assay.ResultsThe results indicated that compounds 4c, 4d and 8c showed growth inhibition activity against HCT-116 with IC50 values of 3.80 ± 0.80, 3.65 ± 0.90 and 3.16 ± 0.90 μM, respectively, compared to harmine (IC50 = 2.40 ± 0.12 μM) and cisplatin (IC50 = 5.18 ± 0.94 μM) reference drugs. Also, compounds 8c, 4d and 4c showed promising IC50 values of 3.47 ± 0.79, 4.13 ± 0.51 and 7.24 ± 0.62 μM, respectively, against the more resistant human colorectal cancer (HT-29) cell line compared with harmine (IC50 = 4.59 ± 0.67 μM) and cisplatin (IC50 = 11.68 ± 1.54 μM). On the other hand, compounds 4d, 4c, 8c and 11c were the most active (IC50 values of 2.31± 0.43, 2.94 ± 0.62, 4.57 ± 0.85 and 9.86 ± 0.78 μM, respectively) against the hepatocellular carcinoma (HepG2) cell line compared with harmine (IC50 = 2.54 ± 0.82 μM) and cisplatin (IC50 = 41 ± 0.63 μM). The study also suggested that the mechanism of the anticancer action exerted by the most active compounds (4c, 4d and 8c) inside HCT-116 cells was apoptosis through the Bcl-2 family.ConclusionThiazole scaffolds 4c, 4d and 8c showed anticancer activities in the micromolar range and are appropriate as a candidate for cancer treatment.

ChemInform Abstract: Phenyl Isothiocyanate in Heterocyclic Synthesis: Novel Synthesis of Thiazoles, Thieno(2,3-b)pyridine, Thiophene and Thieno(3,2-c)pyridazine Derivatives.

The enamino nitriles1 and2 react with phenyl isothiocyanate followed by cyclization with α-haloketones3 and10 to afford in each case the thiazole5, thiophene11 and the thieno[2,3-b]pyridine derivatives19 and21. Chemical and spectroscopic evidences for the structures of the new compounds are described.

ChemInform Abstract: Reactions of Phenyl Isothiocyanate and Sulfur with Dimeric Adducts: Novel Synthesis of Thiazoles, Thiazolo(4,5‐d)pyrimidine and Thiazolo(4, 5‐d)pyridine Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Phenyl isothiocyanate in heterocyclic synthesis: Novel synthesis of thiazoles, thieno[2,3-b]pyridine, thiophene and thieno[3,2-c]pyridazine derivatives

The enamino nitriles1 and2 react with phenyl isothiocyanate followed by cyclization with α-haloketones3 and10 to afford in each case the thiazole5, thiophene11 and the thieno[2,3-b]pyridine derivatives19 and21. Chemical and spectroscopic evidences for the structures of the new compounds are described.

Synthesis of novel thiazoles bearing hydrazine, thiosemicarbazide, thiazole, and thiazolidinone moieties

Thiazolecarboxylate esters (I) and (II) react with hydrazine hydrate to give the acid hydrazides (III) and (IV), which then react with KSCN and PhNCS to give high yields of the thiosemicarbazides (V)-(VIII). Cyclocondensation of the thiosemicarbazide (V) with 3-phenyl-3-chloro-2-oxopropionic acid derivatives gives compounds with two thiazole moieties (IX)-(XIV). The reaction of the phenylthiosemicarbazides (VII) and (VIII) with chloroacetyl chloride and (or) chloroacetic acid affords the thiazolidinonethiazoles (XV) and (XVI).

ChemInform Abstract: A Novel Synthesis of Thiazoles (V) from Dimethyl N‐(Ethoxycarbonylmethyl) Iminodithiocarbonate (IV), Carbon Disulfide (III), and Alkyl Halides (I).

ChemInform Abstract: A Novel Synthesis of Thiazoles (V) from Dimethyl N‐(Ethoxycarbonylmethyl) Iminodithiocarbonate (IV), Carbon Disulfide (III), and Alkyl Halides (I).

ChemInform Abstract: A Novel Synthesis of Thiazoles from S,S‐Dimethyl N‐Ethoxycarbonylmethyliminodithiocarbonate.

AbstractThe title compound (I), a carbon acid, is converted to the thiazoles (IV).

A novel synthesis of thiazoles from dimethyl N-(ethoxycarbonylmethyl)imino dithiocarbonate, carbon disulfide and alkyl halides

We report a new synthesis of thiazoles from a cyclocondensation reaction between dimethyl N-(ethoxycarbonylmethyl)iminodithiocarbonate (EMIC), carbon disulfide and alkylation of intermediate thiazole-2-thiolate with alkyl halides.