374104-63-9

Basic information

• Product Name: 4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE
• Synonyms: THIENO[2,3-D]PYRIMIDINE, 4-CHLORO-5-(4-METHYLPHENYL)-;OTAVA-BB BB7012780012;AURORA 20403;BUTTPARK 82\18-64;4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE;4-CHLORO-5-(4-METHYLPENYL)THIENO[2,3-D]PYRIMIDINE;4-CHLORO-5-(4-METHYLPHENYL)THIENO[2,3-D]PYRIMIDINE
• CAS NO: 374104-63-9
• Molecular Formula: C13H9ClN2S
• Molecular Weight: 260.74
• Mol File: 374104-63-9.mol

Chemical Properties

• Boiling Point: 425.6 °C at 760 mmHg
• Flash Point: 211.2 °C
• Appearance: /
• Density: 1.351 g/cm³
• Vapor Pressure: 4.69E-07mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE(374104-63-9)
• EPA Substance Registry System: 4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE(374104-63-9)

Safety Data

• Hazardous Substances Data: 374104-63-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE is used as a building block for the synthesis of various drugs and pharmaceutical compounds. Its unique structural features and potential pharmacological activities contribute to the development of anti-cancer, anti-inflammatory, and anti-bacterial drugs.
Used in Anti-cancer Applications:
In the field of oncology, 4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE is used as a precursor in the development of anti-cancer drugs. Its potential to target and inhibit specific cancer-related pathways makes it a promising candidate for the creation of novel therapeutic agents.
Used in Anti-inflammatory Applications:
4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE is utilized as a component in the synthesis of anti-inflammatory drugs. Its ability to modulate inflammatory responses and alleviate symptoms associated with inflammation is of interest to researchers and pharmaceutical companies.
Used in Anti-bacterial Applications:
In the development of anti-bacterial drugs, 4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE serves as a key intermediate. Its potential to combat bacterial infections and contribute to the discovery of new antibiotics is significant in the ongoing battle against antibiotic resistance.
Used in Agrochemical Industry:
4-CHLORO-5-P-TOLYL-THIENO[2,3-D]PYRIMIDINE is studied for its potential use as a herbicide and pesticide. Its ability to control the growth of unwanted plants and pests in agricultural settings is being explored, offering a possible solution to enhance crop yields and protect against infestations.

InChI:InChI=1/C13H9ClN2S/c1-8-2-4-9(5-3-8)10-6-17-13-11(10)12(14)15-7-16-13/h2-7H,1H3

Upstream product

• 14505-28-3 ethyl 2?cyano?3?p?tolylbut?2?enoate 
• 122-00-9 para-methylacetophenone 
• 15854-08-7 ethyl 2-amino-4-(4-methylphenyl)thiophene-3-carboxylate 
• 17509-21-6 5-(4-methylphenyl)thieno[2,3-d]pyrimidin-4(3H)-one 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors

The clinical evidence for the success of tyrosine kinase inhibitors in combination with microtubule-targeting agents prompted us to design and develop single agents that possess both epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitory properties. A series of 6-aryl/heteroaryl-4-(3′,4′,5′-trimethoxyanilino)thieno[3,2-d]pyrimidine derivatives were discovered as novel dual tubulin polymerization and EGFR kinase inhibitors. The 4-(3′,4′,5′-trimethoxyanilino)-6-(p-tolyl)thieno[3,2-d]pyrimidine derivative 6g was the most potent compound of the series as an antiproliferative agent, with half-maximal inhibitory concentration (IC50) values in the single- or double-digit nanomolar range. Compound 6g bound to tubulin in the colchicine site and inhibited tubulin assembly with an IC50 value of 0.71 μM, and 6g inhibited EGFR activity with an IC50 value of 30 nM. Our data suggested that the excellent in vitro and in vivo profile of 6g may be derived from its dual inhibition of tubulin polymerization and EGFR kinase.

Identification of 4-methoxythieno[2,3-d]pyrimidines as FGFR1 inhibitors

Aim. To identify novel FGFR1 inhibitors using virtual screening approach. Methods. We used methods of organic synthesis, molecular docking via the Autodock 4.2.6 program package and in vitro biochemical tests with γ-32P. Results. In vitro experiments showed that 9 of 23 tested compounds possess inhibitory activity against FGFR1 with IC50 values in the range from 0.9 to 5.6 μM. Conclusions. Nine FGFR1 inhibitors were developed. The mode of compounds binding with the ATP-acceptor site was determined using molecular docking methods and the dependence of the compounds’ activity on the substituents R1, R4 and R5 was evaluated.

Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines

An extension of our previous research work has resulted in a number of new ATP-competitive CK2 inhibitors that have been identified among 4-aminothieno[2,3-d]pyrimidine derivatives. The most active compounds obtained in the course of the research are 3-(5-p-tolyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5e (NHTP23, IC50 = 0.01 μM), 3-(5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5g (NHTP25, IC50 = 0.065 μM) and 3-(6-methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5n (NHTP33, IC50 = 0.008 μM). Structure-activity relationships of the tested 4-aminothieno[2,3-d]pyrimidine derivatives have been studied and their binding mode with ATP-acceptor site of CK2 has been proposed. A negative effect of intramolecular hydrogen bonding in the compounds' structure is discussed.

Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin- 4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2

A novel series of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids has been synthesized and tested in vitro towards human protein kinase CK2. It was revealed that the most active compounds inhibiting CK2 are 3-{[5-(4-methylphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid and 3-{[5-(4-ethoxyphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid (IC 50 values are 0.1 μM and 0.125 μM, respectively). Structure-activity relationships of 28 tested thienopyrimidine derivatives have been studied and binding mode of this chemical class has been predicted. Evaluation of the inhibitors on seven protein kinases revealed considerable selectivity towards CK2.

SUBSTITUTED AMINOPYRIMIDINES AS NEUROKININ ANTAGONISTS

The invention discloses tachykinin receptor antagonists. The tachykinin family of receptors comprising the neurokinins substance P (SP), neurokinin A, and neurokinin B and related neuropeptides that are widely distributed in the peripheral and central ner

THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS

The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.