59898-68-9

Usage

InChI:InChI=1/C17H16N2OS2/c20-16-14-12-8-4-5-9-13(12)22-15(14)18-17(21)19(16)10-11-6-2-1-3-7-11/h1-3,6-7H,4-5,8-10H2,(H,18,21)

Upstream product

• 59898-53-2 N¹-(3-carbethoxy-4,5,6,7-tetrahydrobenzothien-2-yl)-N²-benzylthiourea 
• 100-46-9 benzylamine 
• 85716-87-6 ethyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 622-78-6 Benzyl isothiocyanate 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 

Relevant academic research and scientific papers

Synthesis, biological evaluation and molecular modeling of novel thienopyrimidinone and triazolothienopyrimidinone derivatives as dual anti-inflammatory antimicrobial agents

New thienopyrimidinone and triazolothienopyrimidinone derivatives have been synthesized. These compounds were subjected to anti-inflammatory and antimicrobial activity screening aiming to identify new candidates that have dual anti-inflammatory and antimicrobial activities. Compounds 5, 7 and 10a showed minimal ulcerogenic effect and high selectivity towards human recombinant COX-2 over COX-1 enzyme. Their docking outcome correlated with their biological activity and assured the high selectivity binding towards COX-2. In addition, they could act safely up to 80 mg/kg orally or 40 mg/kg parentrally. The antimicrobial screening showed that compound 10a displayed distinctive inhibitory effect on the growth of Escherichia coli comparable to that of ampicillin. Moreover, compounds 5, 7, 9 and 12a possessed 50% of the inhibitory activity of ampicillin against E. coli. Thus, compounds 5, 7 and 10a represent promising dual acting anti-inflammatory and antimicrobial agents. This work provides rewarding template enriching the chemical space for dual anti-inflammatory anti-microbial activities.

Synthesis, characterization and cytotoxicity of substituted [1]Benzothieno[3,2-e][1,2,4]triazolo [4,3-a] pyrimidines

A new series of 4-benzyl-6,7,8,9-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidines was synthesized motivated by the widely reported anticancer activity of thieno[2,3-d]pyrimidines and triazolothienopyrimidines. The in vitro cytotoxic activity of some selected compounds was evaluated against two human cell lines: prostate cancer (PC-3) and colon cancer (HCT-116). A preliminary study of the structure-activity relationship of the target compounds was discussed. Most of the synthesized compounds showed remarkable activity on the tested cell lines, while compound 16c had the highest potency against the PC-3 cell line with an IC50 of 5.48 μM compared to Doxorubicin (IC50 = 7.7 μM), the reference standard used in this study. On the other hand, 6c and 18c were the most active against HCT-116 (IC50 = 6.12 and 6.56 μM, respectively) relative to IC50 = 15.82 μM of the standard. Thus, some of the synthesized thienopyri-midine derivatives, specially 6c, 16c and 18c, have the potential to be developed into potent anticancer agents.

Facile synthesis of autophagonizer and evaluation of its activity to induce autophagic cell death in apoptosis-defective cell line

Some cancer cells are resistant to apoptosis, rendering them irresponsive towards apoptosis-inducing chemotherapy drugs. Another mode of action to kill these apoptosis-defective cells is essential and autophagy, a dynamic process that degrades cytoplasmic contents for cellular maintenance, has been considered as one of the alternate routes. A small molecule inducer of autophagy, autophagonizer was reported to induce cell death through a novel process that is independent of extrinsic apoptosis and the normal signaling pathways of autophagy. Here, we describe an efficient synthetic procedure for the autophagonizer. The newly synthesized autophagonizer (DK-1-49) resulted in an accumulation of autophagy-associated LC3-II and enhanced levels of autophagosomes and acidic vacuoles. Furthermore, cell viability was inhibited by autophagic cell death in not only human cancer cells but also Bax/Bak double-knockout cells. These findings highlight that intrinsic apoptosis is not also involved in the induction of cellular death by the autophagonizer suggesting the autophagonizer is a promising candidate for anticancer therapeutics for cancer cells that are resistant to apoptosis-inducing chemotherapy.

Synthesis and transformations of 3-ethoxycarbonyl-2-(N-R-thioreido)thiophenes

3-Ethoxycarbonyl-2-N-R-thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophenes were obtained by the reaction of 2- amino-3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene with isothiocyanates and of 3-ethoxycarbonyl-2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]

Synthesis of 3 substituted thieno[2,3 d]pyrimidin 4(3H) one 2 mercaptoacetic acids and their ethyl esters for pharmacological screening

3 Substituted thieno[2,3 d]pyrimidin 4(3H) one 2 mercaptoacetic acids and their ethyl esters were synthesized from 2 mercaptothieno[2,3 d]pyrimidin 4 (3H) ones, which were obtained by cyclization of thienylthioureas in acidic medium. Analgesic, anti inflammatory, and anticonvulsant activities were found in some of these compounds. Significant antimicrobial activity was exhibited by thienylthioureas.