81765-97-1

Basic information

• Product Name: 4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE
• Synonyms: IFLAB-BB F0307-0219;[1]BENZOTHIENO[2,3-D]PYRIMIDINE, 4-CHLORO-5,6,7,8-TETRAHYDRO-2-METHYL-;4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE;4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE;AKOS 92583;4-Chloro-2-Methyl-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyriMidine, 96%
• CAS NO: 81765-97-1
• Molecular Formula: C₁₁H₁₁ClN₂S
• Molecular Weight: 238.74
• Mol File: 81765-97-1.mol

Chemical Properties

• Melting Point: 94 °C
• Boiling Point: 310.9 °C at 760 mmHg
• Flash Point: 141.8 °C
• Appearance: /
• Density: 1.367 g/cm³
• Vapor Pressure: 0.00106mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.27±0.20(Predicted)
• CAS DataBase Reference: 4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE(81765-97-1)
• EPA Substance Registry System: 4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE(81765-97-1)

Safety Data

• Hazardous Substances Data: 81765-97-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE is used as a reactant for the synthesis of thieno[2,3-d]pyrimidines and furo[2,3-d]pyrimidines derivatives. These derivatives have potential applications as c-Met inhibitors, which are important for the development of antitumor agents. 4-CHLORO-2-METHYL-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE's role in creating these derivatives makes it a valuable component in the advancement of cancer treatment and research.

InChI:InChI=1/C11H11ClN2S/c1-6-13-10(12)9-7-4-2-3-5-8(7)15-11(9)14-6/h2-5H2,1H3

Upstream product

• 19819-15-9 2-methyl-4-hydroxy-5,6,7,8-tetrahydrobenzothieno<2,3-d>pyrimidine 
• 19819-15-9 2-methyl-5,6,7,8-tetrahydrobenzo<4,5>thieno<2,3-d>pyrimidin-4(3H)-one 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 108-94-1 cyclohexanone 

Downstream Products

• 81766-14-5 2-methyl-4-methylthio-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 77995-54-1 4-hydrazinyl-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine 
• 1133824-60-8 N-(4-methoxyphenyl)-N,2-dimethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine 
• 1321618-91-0 N-(3-fluoro-4-(2-methyl-7,8-dihydro-6H-cyclohexa[4.5]thieno[2,3-d]pyrimidin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide 
• 1335636-33-3 C₁₇H₁₆FN₃OS 
• 83548-70-3 4-Methyl-7,8,9,10-tetrahydro-6-thia-1,2,3,3a,5-pentaaza-cyclopenta[c]fluorene 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of 5,6,7,8-Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines as Microtubule Targeting Agents

A series of eleven 4-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines were designed and synthesized and their biological activities were evaluated. Synthesis involved the Gewald reaction to synthesize ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate ring, and SNAr reactions. Compound 4 was 1.6-and ~7-fold more potent than the lead compound 1 in cell proliferation and microtubule depolymerization assays, respectively. Compounds 4, 5 and 7 showed the most potent antiproliferative effects (IC50 values 50 values of 53–125 nM). Additionally, compounds 4–8, 10 and 12–13 circumvented Pgp and βIII-tubulin mediated drug resistance, mechanisms that diminish the clinical efficacy of paclitaxel (PTX). In the NCI-60 cell line panel, compound 4 exhibited an average GI50 of ~10 nM in the 40 most sensitive cell lines. Compound 4 demonstrated statistically significant antitumor effects in a murine MDA-MB-435 xenograft model.

Synthesis and anthelmintic activity of some novel (E)-2-methyl/propyl-4-(2-(substitutedbenzylidene)hydrazinyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines

A series of some novel (E)-2-methyl/propyl-4-[(2-(substitutedbenzylidene)hydrazinyl]-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines was synthesized and characterized by adopting an appropriate synthetic scheme. The effect of electron withdrawing and

5,6,7,8-Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine derivatives as inhibitors of full-length RORγt

Retinoid-related orphan receptor gamma-t (RORγt) belongs to the nuclear receptor superfamily that takes vital roles in the development and maturation of T-helper 17 cell (Th17) and lymph-node genesis. Because Th17 cells have been proved to be major effectors in human autoimmune and inflammatory diseases, the agonists and antagonists of RORγt have been discovered as promising leads for the therapeutics of these diseases. Most of the current studies of RORγt inhibitors have been focused on ligand binding domain (LBD) of RORγt because the structure and binding pockets of LBD have been elucidated and studied in detail. Recent research elucidated that the hinge domain (HD) of RORγt was significantly involved in the SUMOylation of RORγt and thus specifically affecting T cell development but not lymph-node genesis. These discoveries highlighted the potential of HD of RORγt as the target of RORγt inhibitors that could specifically inhibit Th17-related activities without affecting lymph-node genesis. In this study, we utilized a screening system with full-length RORγt including DBD, HD and LBD to evaluate the activities of a synthesized library of tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine derivatives. We identified a potent lead compound (28) that effectively inhibited Th17 cell differentiation. Docking and structure–activity relationship (SAR) studies showed that compound 28 may not bind in the binding pocket as most of the known inhibitors, but may bind in the pocket closed to Gln223 and Leu244 in HD. Our studies showed evidence that the HD of RORγt could afford a binding pocket for Th17 specific inhibitors and this domain should be further studied to discover potent and specific RORγt inhibitors.

Computer-aided identification, synthesis and evaluation of substituted thienopyrimidines as novel inhibitors of HCV replication

A structure-based virtual screening technique was applied to the study of the HCV NS3 helicase, with the aim to find novel inhibitors of the HCV replication. A library of ～450000 commercially available compounds was analysed in silico and 21 structures were selected for biological evaluation in the HCV replicon assay. One hit characterized by a substituted thieno-pyrimidine scaffold was found to inhibit the viral replication with an EC50value in the sub-micromolar range and a good selectivity index. Different series of novel thieno-pyrimidine derivatives were designed and synthesised; several new structures showed antiviral activity in the low or sub-micromolar range.

Multistep, microwave assisted, solvent free synthesis and antibacterial activity of 6-substituted-2,3,4-trihydropyrimido[1,2-c]9,10,11,12- tetrahydrobenzo[b]thieno[3,2-e]pyrimidines

A novel, efficient, microwave assisted route for the synthesis of 6-substituted-2,3,4-trihydropyrimido[1,2-c]-9,10,11,12-tetrahydrobenzo[b] thieno[3,2-e]pyrimidines in good yields has been developed. The intermediates, 2-substituted-4-[3-hydroxy(propyl-1-

Microwave-Assisted Synthesis of Novel 5-Substituted-2,3-dihydroimidazo[1,2-c]thieno[3,2-e]pyrimidines

A novel, facile microwave-assisted route for the synthesis of imidazo[1,2-c]thieno[3,2-e]pyrimidines 4 in quantitative yields is reported. The intermediates 4-chlorothieno[2,3-d]pyrimidines 3 were synthesized under one-pot reaction conditions.

Synthesis and Biological Activity of Tetrazolothienopyrimidines

4-Hydrazinothienopyrimidines (VI) undergo cyclization with nitrous acid to give tetrazolothienopyrimidines (VII).The latter compounds have been screened for their analgesic and antiinflammatory activities.

3,4-Dihydrothienopyrimidines. II. Synthesis and Sodium Borohydride Reduction of 2-Substituted 4-Chloro- and 4-Unsubstituted-thienopyrimidines

The synthesis and sodium borohydride reduction of 4-chloro- (1) and 4-unsubstituted- (3) 5,6,7,8-tetrahydrobenzothienopyrimidines, substituted with various groups, such as chloro, hydrogen, methyl, phenyl, amino, ethoxy, methylthio, methylsulfin