40493-18-3

Basic information

• Product Name: 4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE
• Synonyms: [1]BENZOTHIENO[2,3-D]PYRIMIDINE, 4-CHLORO-5,6,7,8-TETRAHYDRO-;AKOS 92587;AKOS BBS-00004607;AKOS USSH-4110760;4-CHLORO-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDINE;4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE;IFLAB-BB F1126-0518;BUTTPARK 59\40-36
• CAS NO: 40493-18-3
• Molecular Formula: C₁₀H₉ClN₂S
• Molecular Weight: 224.71
• Mol File: 40493-18-3.mol
• Article Data: 49

Chemical Properties

• Melting Point: 228℃ (N,N-dimethylformamide water )
• Boiling Point: 377.2 °C at 760 mmHg
• Flash Point: 181.9 °C
• Appearance: /
• Density: 1.419 g/cm³
• Vapor Pressure: 1.49E-05mmHg at 25°C
• Refractive Index: 1.687
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE(40493-18-3)
• EPA Substance Registry System: 4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE(40493-18-3)

Safety Data

• Hazardous Substances Data: 40493-18-3(Hazardous Substances Data)

Usage

General Description

4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE is a chemical compound with a molecular formula C11H8ClN3S. It is a heterocyclic compound that contains a benzothiophene ring fused to a pyrimidine ring. 4-CHLORO-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-D]PYRIMIDINE is also referred to as a benzo[b]thieno[4,5-d]pyrimidine derivative and is used in the synthesis of pharmaceutical compounds and as a building block in organic chemistry. It has potential applications in the development of new drugs and active pharmaceutical ingredients due to its unique structural and chemical properties.

InChI:InChI=1/C10H9ClN2S/c11-9-8-6-3-1-2-4-7(6)14-10(8)13-5-12-9/h5H,1-4H2

Upstream product

• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 51550-17-5 5,6,7,8-tetrahydro-2-(methylthio)<1>benzothieno<2,3-d>pyrimidin-4(1H)-one 
• 14770-79-7 2-amino-4,5,6,7-tetrahydrobenzothiophene 
• 4651-91-6 3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene 
• 108354-78-5 methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 5936-58-3 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 77287-34-4 formamide 
• 108-94-1 cyclohexanone 
• 14346-24-8 8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1⁽⁹⁾,2⁽⁷⁾,3,5-tetraen-3-ol 
• 81765-98-2 4-chloro-2-methylthio-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 4815-28-5 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 81766-01-0 4-chloro-2-mesyl-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 81766-00-9 4-chloro-2-methylsulfinyl-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 14346-24-8 5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 

Downstream Products

• 70059-63-1 (2-fluoro-phenyl)-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine 
• 40277-52-9 4-phenoxy-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine 
• 40277-42-7 4-phenylsulfanyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine 
• 4994-88-1 5,6,7,8-tetrahydrobenzo[b]thiopheno[2,3-d]pyrimidin-4-ylamine 
• 40106-45-4 4-hydrazino-5,6-tetramethylenothieno<2,3-d>pyrimidine 
• 70059-61-9 (4-chloro-benzyl)-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine 
• 70059-62-0 (2,4-dichloro-benzyl)-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine 
• 70059-60-8 (2-chloro-benzyl)-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine 
• 14346-24-8 5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 81136-48-3 4-(3-methoxyphenyl)amino-5,6-tetramethylenothieno<2,3-d>pyrimidine 
• 81136-46-1 4-(3,5-dimethylphenyl)amino-5,6-tetramethylenothieno<2,3-d>pyrimidine 
• 81136-47-2 4-(2-methylphenyl)amino-5,6-tetramethylenothieno<2,3-d>pyrimidine 
• 40277-39-2 4-mercapto-5,6-tetramethylenethieno<2,3-d>pyrimidine 
• 362509-18-0 4-(3-chloro-4-fluoroanilino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine 

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.

Structure based design, synthesis and evaluation of new thienopyrimidine derivatives as anti-bacterial agents

TrmD, tRNA-(N1G37) methyltransferase, a member of SpoU-TrmD (SPOUT) RNA methyltransferase family, is one of the key enzymes responsible for the growth of Staphylococcus aureus, Pseudomonas aeruginosa, Mycobacterium tuberculosis (Mtb) and Mycobacterium abscessus (Mab). A number of TrmD inhibitors including thienopyrimidines and fused thienopyrimidines are reported as potent anti-bacterial and anti-mycobacterial agents. In the current study, a library of ~200 structurally diverse thienopyrimidines were designed and subjected to preliminary in silico studies. 22 of the compounds were selected, synthesized and were evaluated for their inhibitory activities against a panel of pathogens consisting E. coli, S. aureus, K. pneuminiae, A. baumannii and P. aeruginosa and M. tuberculosis (ATCC 27294). Among the tested compounds, 13b, 18a-e were found to inhibit M. tuberculosis (ATCC 27294) with the MIC of 16-32 μg/mL. The compound 18f was found to be selective against S. aureus with the MIC of 4 μg/mL and moderate activity against M. tuberculosis. The selected compounds were further subjected to docking, 3D-QSAR and ADME/T studies to understand the mechanism of action and also their physico chemical profile.

Synthesis of New Thieno[2,3-d]pyrimidines Containing a 1,2,3-Triazole Ring and Their Therapeutic Response in NCI-60 Cell Line Panel

Abstract: A series of new tetrahydro[1]benzothieno[2,3-d]pyrimidines containing a 1,2,3-triazole fragment linkedthrough an oxymethylene spacer have been synthesized by click reaction of4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidines with various aryl and alkyl azides inthe presence of copper sulfate and sodium ascorbate as a catalyst. Thestructures of the synthesized compounds were characterized by variousspectroscopic techniques (1H and13C NMR, FT-IR, and mass spectrometry), and theirin vitro anticancer activity against NCI-60 human tumor cell lines wasevaluated. Among the compounds tested, N-(pyridine-3-yl)-acetamide derivative exhibited significantactivity against several cancer cell lines, including SF-539 (CNS cancer),HCT-116 (colon cancer), OVCAR-8 (ovarian cancer), PC-3 (prostate cancer), andCCRF-CEM (leukemia).