182198-35-2

Basic information

• Product Name: 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE
• Synonyms: 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE;AKOS 90534;AKOS NCG-0083;AKOS BBS-00006350;BUTTPARK 30\08-39;THIENO[2,3-D]PYRIMIDINE, 4-CHLORO-5-PHENYL-;OTAVA-BB BB7012780011
• CAS NO: 182198-35-2
• Molecular Formula: C₁₂H₇ClN₂S
• Molecular Weight: 246.72
• Mol File: 182198-35-2.mol

Chemical Properties

• Melting Point: 130°C
• Boiling Point: 418.9 °C at 760 mmHg
• Flash Point: 207.1 °C
• Appearance: /
• Density: 1.396 g/cm³
• Vapor Pressure: 7.73E-07mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: 2-8°C
• PKA: 0.34±0.40(Predicted)
• CAS DataBase Reference: 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE(182198-35-2)
• EPA Substance Registry System: 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE(182198-35-2)

Safety Data

• Hazardous Substances Data: 182198-35-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE is utilized as a key intermediate in the synthesis of pharmaceutical compounds for its potential to contribute to the development of new drugs. Its unique structure allows for the exploration of various biological activities, making it instrumental in medicinal chemistry for creating novel therapeutic agents.
Used in Agrochemical Research:
In the agrochemical industry, 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE is employed as a building block for the creation of crop protection products. Its chemical properties are harnessed to develop new pesticides or herbicides, enhancing agricultural productivity and crop protection strategies.
Used in Chemical Synthesis:
4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE serves as a vital component in chemical synthesis processes, particularly for the production of complex organic molecules with potential applications in various industries. Its reactivity and structural features make it a preferred choice for synthesizing compounds with specific therapeutic or functional properties.
Used in Medicinal Chemistry Research:
4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE is applied as a subject of study in medicinal chemistry research to understand its interactions with biological targets and its potential to modulate biological processes. This research is crucial for identifying new drug candidates and optimizing their efficacy and safety profiles.

InChI:InChI=1/C12H7ClN2S/c13-11-10-9(8-4-2-1-3-5-8)6-16-12(10)15-7-14-11/h1-7H

Upstream product

• 35978-39-3 5-phenylthieno<2,3-d>pyrimidine-4(3H)one 
• 100-52-7 benzaldehyde 
• 14533-92-7 ethyl 2-cyano-3-phenylbut-2-enoate 
• 98-86-2 acetophenone 
• 35978-39-3 5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one 
• 4815-36-5 ethyl 2-amino-4-phenyl-thiophene-3-carboxylate 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 

Downstream Products

• 182198-50-1 2-(5-Phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-ethanol 
• 113246-86-9 4-Hydrazino-5-phenylthieno<2,3-d>pyrimidine 
• 182198-89-6 5-Phenyl-thieno[2,3-d]pyrimidine-4-thiol 
• 113246-89-2 9-Phenyl-1,2,4-triazolo<4,3-c>thieno<3,2-e>pyrimidine 
• 117562-88-6 9-phenyl-1,2,3,4-tetrazolo<5,1-f>thieno<2,3-d>pyrimidine 
• 182199-66-2 3-Methyl-9-phenylthieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine 
• 182199-17-3 9-Phenyl-2H-thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine-3-thione 
• 182198-99-8 N-[1-Phenyl-meth-(E)-ylidene]-N'-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-hydrazine 

Relevant articles and documents

Design, molecular docking and biological evaluation of fused thienopyrimidines and quinazoline

The anticancer activity of the condensed pyrimidine and quinazoline moieties are pronounced with a different pathway. Thienopyrimidine is considered as ring equivalent bioisosteres of quinazolines and present in other heterocyclic compounds including thienopyrimidine. The present investigation focused on the synthesis of thienopyrimidine and quinazoline derivatives for their anticancer activity against the human oral squamous carcinoma-3 (HSC-3) cell line. The synthesized compound confirmed for their structural characteristics from spectral analysis and tested for anti-proliferative activity from MTT assay. The electron-withdrawing group in 4-chloro thienopyrimidines and amino ester derivate/facilitate the inhibition of cancer cells. Further probing by docking studies revealed that the compounds exhibit possible interactions with VEGF, FGFR and c-Met proteins, which are known to have a role in the pathogenesis of oral squamous cell carcinoma. Among the derivatives a moderate activity demonstrated by substituted 4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]-pyrimidine (4a) and ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (1a) derivatives. Lack of chirality and the presence of bulky substituents in few of the compounds were found to be the cause for lower potency.

ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF

Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor

We recently described a structurally novel series of negative allosteric modulators (NAMs) of the dopamine D2 receptor (D2R) based on thieno[2,3-d]pyrimidine 1, showing it can be structurally simplified to reveal low molecular weight, fragment-like NAMs that retain robust negative cooperativity, such as 3. Herein, we report the synthesis and functional profiling of analogues of 3, placing specific emphasis on examining secondary and tertiary amino substituents at the 4-position, combined with a range of substituents at the 5/6-positions (e.g. aromatic/aliphatic carbocycles). We identify analogues with diverse pharmacology at the D2R including NAMs with sub-μM affinity (9h) and, surprisingly, low efficacy partial agonists (9d and 9i).

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.

Polysubstituted quinolone compounds, and preparation method and use thereof

The invention provides polysubstituted quinolone compounds, and a preparation method and a use thereof, and concretely provides a polysubstituted quinolone compound represented by formula I, and optical isomers, pharmaceutically acceptable salts or solvates thereof. All groups in the formula I are defined in the description. The quinolone compound has excellent c-Met inhibition activity, and can be used for treating c-Met activity or expression level corrected diseases.

4-Substituted thieno[2,3-d]pyrimidines as potent antibacterial agents: Rational design, microwave-assisted synthesis, biological evaluation and molecular docking studies

In an attempt to discover a new class of antibacterial agents with improved efficacy and to overcome the drug-resistant problems, some novel 4-substituted thieno[2,3-d]pyrimidines have been synthesized via microwave-assisted methodology and evaluated for their in vitro antibacterial activity against various pathogenic bacterial strains. Compounds 12b and 13c showed the promising inhibitory potencies against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli with MICs ranging from 2 to 10?μg/ml. Compound 13c was also found to be highly potent against methicillin-resistant S. aureus (MRSA) with MIC value of 4?μg/ml. Docking simulation studies have been performed to unravel the mode of action and association study indicate the binding of potent compounds with DHPS enzyme. In silico ADME studies suggest the drug-like characteristics of the potent compounds.

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.

Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization

Resulting from a vHTS based on a pharmacophore alignment on known β3-adrenoceptor ligands, an aryloxypropanolamine scaffold comprising a thienopyrimidine moiety was further optimized as a human β3-AR agonist, yielding a lead compound with an excellent cellular activity of EC50 = 20 pM, selectivity over hβ1- and hβ2-adrenoceptors and a promising safety profile.

Aryloxypropanolamines, methods of preparation thereof and use of aryloxypropanolamines as medicaments

This invention relates to novel aryloxypropanolamines. The invention also relates to the pharmaceutically acceptable salts and solvates containing said compounds, methods for the preparation thereof and to respective synthesis intermediates. Said compound