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Abstract
Novel tetrahydrobenzo[b]thienopyrole derivatives are synthesized from 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene (1) through its reaction with α-chloroacetone to give the corresponding N-alkyl derivative 3. Compound 3 undergoes ready cyclization in sodium ethoxide solution to give the tetrahydrobenzo[b]thienopyrrole 4. The latter compound 4 is used as the key starting material for the synthesis of thiophene, thieno[2,3-b]pyridine and pyran derivatives. The cytotoxicity of the synthesized products towards the human cancer cell lines namely gastric cancer (NUGC), colon cancer (DLD-1), liver cancer (HA22T and HEPG-2), breast cancer (MCF-7), nasopharyngeal carcinoma (HONE-1) and normal fibroblast (WI-38) cell lines are measured. Compounds 4, 7a, 7b, 8a, 8b, 10c, 10d, 10f, 12a, 12b, 14b and 15b exhibit the optimal cytotoxic effect against cancer cell lines. Compounds 7b and 14b show the maximum inhibitory effect and these are much higher than the reference CHS-828 (pyridyl cyanoguanidine). On the other hand, the anti-proliferative evaluations of these compounds with high potency against the cancer cell lines L1210, Molt4/C8, CEM, K562, K562/4 and HCT116 show that compounds 7b and 8b give IC50's against Molt4/C8 and CEM cell lines higher than that of the reference, doxorubicin.
Highlights
Sulfur containing heterocycles paved way for the active research in the pharmaceutical Chemistry
A large number of compounds containing thiophene system have been investigated because of their broad spectrum of biological activities which include analgesic,4 antibacterial,5 antifungal,6 antiparasitic,7 antiviral,8 anti-inflammatory,9 anticonvulsant,10 anti-nociceptive,11 DNA cleavage,12 herbicidal,13 antitubercular,14 protein kinase inhibition,15 respiratory syndrome protease inactivation,16 an active ester in the peptide synthesis and agonists of peroxisome proliferator activated receptors
Our research group was involved through comprehensive program aiming for the synthesis of 4,5,6,7-tetrahydrobenzo[b]thiophene derivatives followed by their antitumor evaluations
Summary
Sulfur containing heterocycles paved way for the active research in the pharmaceutical Chemistry. A large number of compounds containing thiophene system have been investigated because of their broad spectrum of biological activities which include analgesic, antibacterial, antifungal, antiparasitic, antiviral, anti-inflammatory, anticonvulsant, anti-nociceptive, DNA cleavage, herbicidal, antitubercular, protein kinase inhibition, respiratory syndrome protease inactivation, an active ester in the peptide synthesis and agonists of peroxisome proliferator activated receptors.. A large number of compounds containing thiophene system have been investigated because of their broad spectrum of biological activities which include analgesic, antibacterial, antifungal, antiparasitic, antiviral, anti-inflammatory, anticonvulsant, anti-nociceptive, DNA cleavage, herbicidal, antitubercular, protein kinase inhibition, respiratory syndrome protease inactivation, an active ester in the peptide synthesis and agonists of peroxisome proliferator activated receptors.17 In addition to these considerable biological applications, tetrahydrobenzo[b]thiophenes are important intermediates, protecting groups and final products in organic synthesis. Our research group was involved through comprehensive program aiming for the synthesis of 4,5,6,7-tetrahydrobenzo[b]thiophene derivatives followed by their antitumor evaluations. we reported the multi-component reactions with 3-(α-bromoacetyl)coumarin to give pyan and pyrididine derivatives. In continuation of this program we are demonstrating the use of 2-amino-3-cyano4,5,6,7-tetrahydrobenzo[b]thiophene for the synthesis of tetrahydrobenzo[b]thienopyrrole derivatives followed by their cytotoxic and the anti-proliferative evaluations.
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