Synthesis and Anti‐cancer Activity of 1,3,4‐Thiadiazole and 1,3‐Thiazole Derivatives Having 1,3,4‐Oxadiazole Moiety

Abstract

in Wiley Online Library (wileyonlinelibrary.com).Reaction of 1,3,4-oxadiazolyl-phenylthiourea 3 with hydrazonoyl halides gave the corresponding 1,3,4oxadiazolylimino-1,3,4-thiadiazoles. Also, treatment of 3 with ethyl chloroacetate and α-haloketones afforded the corresponding thiazolidinone and thiazole derivatives, respectively. The structures of the synthesized products were confirmed by spectral data. Ten compounds were evaluated for their anti-cancer activity against the colon carcinoma cell line . The results revealed that 1,3,4-thiadiazole derivatives 13d and 19c (IC 50 = 0.73 and 0.86 μg/mL, respectively) have promising antitumor activity against colon carcinoma , and most of the tested compounds showed moderate anti-cancer activity. Scheme 1. Synthesis of 1-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-3-phenylthiourea 3. Scheme 2. Reaction of 3 with N′-phenylbenzohydrazonoyl chloride 4. Scheme 3. Reaction of 3 with 2-oxo-N′-arylpropanehydrazonoyl chloride 9a-f. Scheme 4. Reaction of 3 with 2-oxo-N′-phenyl-2-(arylamino)acetohydrazonoyl chloride 17a-c. Scheme 5. Reaction of 3 with α-halocarbonyl compounds 21 and 23a,b.

Ethyl 7-Methyl-1-(4-nitrophenyl)-5-phenyl-3-(thiophen-2-yl)-1,5-dihydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate

“…The 13 C-NMR spectrum provided the expected number and types of carbons. It showed five characteristic signals at δ = 13.8 (CH 3 Encouraged by the above observations and in continuation of our previous work on the synthesis of antitumor agents [17][18][19][20][21], the synthesis of a 1,2,4-triazolopyrimidine, incorporating the thiophene moiety as a promising antitumor agent, was planned, using N-(4-nitrophenyl)thiophene-2-carbohydrazonoyl chloride as a versatile building block.…”

“…Encouraged by the above observations and in continuation of our previous work on the synthesis of antitumor agents [17][18][19][20][21], the synthesis of a 1,2,4-triazolopyrimidine, incorporating the thiophene moiety as a promising antitumor agent, was planned, using N-(4-nitrophenyl)thiophene-2-carbohydrazonoyl chloride as a versatile building block. the growth of a wide range of cancer cell lines including leukemia and prostate and lung cancer at low dose levels [15].…”

Synthesis and characterizations of novel thiazolyl-thiadiazole derivatives as telomerase activators

“…Relative telomerase activity ± SE TDA 7 2.53 ± 0.14 TDA 8 3.21 ± 0.15* TDA 14 2.6 ± 0.14 TDA 15 2.67 ± 0.21 TDA 16 2.16 ± 0.14 Control (vehicle/DMSO) 2.36 ± 0.14 *Statistically different from vehicle (P < 0.05).…”

Synthesis, Characterization, and Antifungal Activity Evaluation of Some Novel Arylazothiazoles

“…Antimicrobial screening studies pointed out that variously 2-[3-methyl-2,6-disubstituted piperidin-4-hydrazono]-1,3-thiazolidin-4-ones have promising activities against Staphylococcus aureus, Rhizopus sp., and Klebsiella pneumoniae and showed twofold improved potency than ciprofloxacin and amphotericin B reference drugs [12] From the previous findings and as a part of an ongoing research program on synthesis of bioactive thiazoles [13][14][15][16][17][18][19][20][21][22], we are interested herein to synthesize a new series of 2-(2-(1-methylpiperidin-4-ylidene)hydrazinyl)-4-substituted-5-(aryldiazenyl)thiazole derivatives to investigate their antidermatophtic activity.…”