One‐pot solvent‐free synthesis of novel functionalized ethyl 2‐(alkylimino)‐4‐methyl‐3‐(alkanoyl)‐2,3‐dihydrothiazole‐5‐carboxylates

Chavan

et al. 2018

J Chinese Chemical Soc

A series of novel thiazol-2-yl substituted-1-sulfonamide derivatives were synthesized from anilines. This involved the coupling of sulfonyl chlorides with thiazol amine to obtain the final compounds 7a-7j and 8a-8j. All synthesized compounds were screened for anticancer activity against MCF-7, HeLa, A-549, and Du-145 cancer cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Preliminary bioassay suggests that most of the compounds show anti-proliferation to different degrees, with doxorubicin used as positive control. The synthesized compounds show IC 50 values in the range 2.74-8.17 μM in the different cell lines. The compounds 7d, 7e, 8a, 8d, and 8e were active compared to doxorubicin. The compounds having butyl and pantyl chains were more active than their lower and higher carbon chains and also their ring counterparts.

Section: Resultsmentioning

confidence: 99%

Synthesis, anti‐proliferative activity, SAR, and kinase inhibition studies of thiazol‐2‐yl‐ substituted sulfonamide derivatives

Chavan

et al. 2018

J Chinese Chemical Soc

“…Recently, 2‐amino‐4‐arylthiazoles were explored in detail as “prodrugs” for the treatment of type‐2 diabetes, tuberculosis, and Parkinson's disease . A variety of methods have been reported for the synthesis of thiazole derivatives from α‐bromoketones, simple ketones, and other substrates . Most of them suffer from the use of lacrymatory α‐bromoketones and their availability, narrow substrate scope, use of volatile and toxic solvents, low yields, tedious work‐up procedures, and identification/preparation of a suitable catalyst.…”

Section: Introductionmentioning

confidence: 99%

Citric Acid‐catalyzed Synthesis of 2,4‐Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach

Godugu

Reddy

2017

J Chinese Chemical Soc

An improved and greener protocol has been developed for the synthesis of 2,4‐disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N‐bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α‐bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large‐scale synthesis.

“…另外, 化合物 III 可作为大麻素受体配体 [3] , 2-酰基亚甲基-3-甲基噻唑啉(IV)具有潜在的治疗类风湿性关节炎和其他炎症的作用 [4] (图 1). 目前该类化合物的合成方法研究较少 [5] , 因此建立新的简单、高效的噻唑啉衍生物合成方法具有重要意义.…”

unclassified

Tetrabutylammonium Iodide/t-Butylhydroperoxide Catalytic/Oxidative Synthesis of Thiazolylidene Derivatives

Yu¹,

Liu²,

Li³

2017

Chin. J. Org. Chem.

A novel method based on reaction of β-ketothioamides (KTAs) with malononitrile to construct thiazolylidenes has been developed under metal-free conditions. This method used cheap tetrabutylammonium iodide (TBAI) as catalyst and t-butylhydroperoxide (TBHP) as oxidant in the presence of Et 3 N at room temperature for 1 h to synthesize a series of 4-aminothiazolylidene derivatives in good yields. This reaction has some advantages such as simple operation, mild reaction conditions, short reaction time, environmentally benign and simple work-up. Keywords thiazolylidenes; β-ketothioamides; TBAI/TBHP; catalysis 噻唑啉类化合物在生物和医药等领域都有重要应用, 与许多生物酶或受体结合表现出多种生物活性 [1] . 例如, Pyochelin (I)不仅是微生物的铁载体而且具有抗肿瘤活性 [2a] , Didehydromirabazole A (II)对实体瘤具有特异选择性, 同时还具有广谱抗肿瘤活性 [2b] . 另外, 化合物 III 可作为大麻素受体配体 [3] , 2-酰基亚甲基-3-甲基噻唑啉(IV)具有潜在的治疗类风湿性关节炎和其他炎症的作用 [4] (图 1). 目前该类化合物的合成方法研究较少 [5] , 因此建立新的简单、高效的噻唑啉衍生物合成方法具有重要意义.