Abstract
2-(3-(1H-Indol-3-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-substituted-5-(substituted diazenyl)thiazoles and 2-(1H-indol-3-yl)-9-substituted-4,7-disubstituted pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(7H)-ones were synthesized via reaction of hydrazonoyl halides with each of 3-(1H-indol-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide and 7-(1H-indol-3-yl)-2- thioxo-5-substituted-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ones, respectively. Also, hydrazonoyl halides were reacted with N’-(1-(1H-indol-3-yl)ethylidene)-2-cyanoacetohydrazide to afford 1,3,4-thiadiazole derivatives. Structures of the new synthesis were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Fifteen of the new compounds have been evaluated for their antitumor activity against the MCF-7 human breast carcinoma cell line. The results indicated that many of the tested compounds showed moderate to high anticancer activity when compared with doxorubicin as a reference drug.
Highlights
The wide-ranging biological activity associated with indole derivatives, both naturally occurring and synthetic, ensures that the synthesis of indole derivatives remains a topic of current interest [1,2,3,4]
Thiazoles can be found in drug development for the treatment of allergies [7], hypertension [8], inflammation [9], schizophrenia [10], bacterial infections [11], HIV [12], sleep disorders [13], and for the treatment of pain [14], as fibrinogen receptor antagonists with antithrombotic activity [15] and as new inhibitors of bacterial DNA gyrase B [16]
16, spiro intermediate and thiohydrazide did not succeed, even under elucidated by elemental analysis and spectral data. Mild conditions as they readily undergo in situ cyclization followed by elimination of hydrogen sulfide to give the final product 19. This structural assignment is consistent with literature reports, which indicate that reaction of hydrazonoyl halides with 2-thioxo-pyrimidin-4-one yielded regioselectively the corresponding 1,2,4-triazolo[4,3-a]pyrimidin- 5-one derivatives [42]
Summary
The wide-ranging biological activity associated with indole derivatives, both naturally occurring and synthetic, ensures that the synthesis of indole derivatives remains a topic of current interest [1,2,3,4]. B viral, antileishmanial, anti-inflammatory, analgesic, CNS depressant, anticancer, antioxidant, antidiabetic, molluscicidal, antihypertensive, diuretic, analgesic, antimicrobial, antitubercular, and anticonvulsant activities [23,24,25,26,27,28,29,30,31,32] In light of these facts, we have synthesized some new thiazole, dihydropyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidine and 1,3,4-thiadiazole derivatives using. Molecules 2016, 21, 929; doi:10.3390/molecules21070929 www.mdpi.com/journal/molecules thiazole and 1,3,4‐thiadiazole have antitumor activity with excellent IG50 and IC50 as depicted in Figure 1 [33,34,35,36,37] In view of these facts, we report the synthesis of a new series of thiazoles and.
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