181374-43-6

Basic information

• Product Name: 2,4-dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyriMidine
• Synonyms: 2,4-dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyriMidine;2,4-dichloro-5H,7H,8H-thiopyrano[4,3-d]pyrimidine
• CAS NO: 181374-43-6
• Molecular Formula: C₇H₆Cl₂N₂S
• Molecular Weight: 221.10694
• Product Categories: pyrimidine;Heterocycle-Pyrimidine series
• Mol File: 181374-43-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 385.2°C at 760 mmHg
• Flash Point: 186.8°C
• Appearance: /
• Density: 1.513
• Vapor Pressure: 8.56E-06mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2,4-dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyriMidine(181374-43-6)
• EPA Substance Registry System: 2,4-dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyriMidine(181374-43-6)

Safety Data

• Hazardous Substances Data: 181374-43-6(Hazardous Substances Data)

Usage

General Description

2,4-Dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine is a chemical compound that belongs to the class of thiopyrano pyrimidines. It is a heterocyclic compound containing both sulfur and nitrogen atoms in its structure. This chemical is known for its potential biological activities, including antitumor and anti-inflammatory properties. It has been studied for its potential use in pharmaceutical applications, and its structure and properties make it a promising candidate for further research and development.

InChI:InChI=1/C7H6Cl2N2S/c8-6-4-3-12-2-1-5(4)10-7(9)11-6/h1-3H2

Upstream product

• 857956-61-7 7,8-dihydro-1H-thiopyrano[4,3-d]pyrimidine-2,4(3H,5H)-dione 
• 4131-74-2 Dimethyl 3,3'-thiodipropionate 
• 857956-61-7 7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine-2,4-diol 
• 4160-61-6 3-methoxycarbonyltetrahydropyran-4-one 

Downstream Products

• 1393712-18-9 PF-05139962 

Relevant articles and documents

Discovery of Novel Dihydrothiopyrano[4,3-d]pyrimidine Derivatives as Potent HIV-1 NNRTIs with Significantly Reduced hERG Inhibitory Activity and Improved Resistance Profiles

Enlightened by the available structural biology information, a novel series of dihydrothiopyrano[4,3-d]pyrimidine derivatives were rationally designedviascaffold hopping and molecular hybridization strategies. Notably, compound 20a yielded exceptionally potent antiviral activities (EC50= 4.44-54.5 nM) against various HIV-1 strains and improved resistance profiles (RF = 0.5-5.6) compared to etravirine and rilpivirine. Meanwhile, 20a exhibited reduced cytotoxicity (CC50= 284 μM) and higher SI values (SI = 5210-63992). Molecular dynamics simulations were performed to rationalize the distinct resistance profiles. Besides, 20a displayed better solubility (sol. = 12.8 μg/mL) and no significant inhibition of the main CYP enzymes. Furthermore, 20a was characterized for prominent metabolic stability andin vivosafety properties. Most importantly, the hERG inhibition profile of 20a (IC50= 19.84 μM) was a remarkable improvement. Overall, 20a possesses huge potential to serve as a promising drug candidate due to its excellent potency, low toxicity, and favorable drug-like properties.

Design, synthesis, biological evaluation and docking studies of novel 2-substituted-4-morpholino-7,8-dihydro-5 H -thiopyrano[4,3- d ]pyrimidine derivatives as dual PI3Kα/mTOR inhibitors

Four series of 2-substituted-4-morpholino- 7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine derivatives (9-28) were designed, synthesized and their structures were confirmed by 1H NMR, 13C NMR and MS spectrum. All compounds were evaluated for the IC50 values against three cancer cell lines (A549, PC-3 and MCF-7). And four selected compounds (10, 11, 24, 27) were further evaluated for the IC50 values against PI3Kα and mTOR kinases. Seven of the target compounds exhibited moderate to excellent antitumor activities against these three cancer cell lines. The most promising compound 11 showed good antitumor potency for A549, PC-3 and MCF-7 cell lines with IC50 values of 0.52 ± 0.10 1/4M, 1.41 ± 0.10 1/4M, 4.82 ± 0.24 1/4M and moderate antitumor activities against PI3Kα/mTOR with IC50 values of 6.72 ± 0.30 1/4M and 0.94 ± 0.10 1/4M. Structure-activity relationships (SARs) and docking studies indicated that aryl urea scaffolds had a significant impact on the antitumor activities, and aryl pyridine urea scaffolds produced the best potency. Variations in substitutions of the aryl group had a significant impact on the activity and 3-Cl-4-F or 3-CF3-4-Cl substitution was more preferred.

Design, synthesis, anticancer activity and docking studies of novel 4-morpholino-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine derivatives as mTOR inhibitors

A series of 7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine derivatives (7a-q, 10a-q) were designed, synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR, MS and HRMS spectrum. All the compounds were evaluated for t

Preparation and application of 2-aminopyrimidine heterocyclic compounds containing 4-acylamino phenoxy

The invention relates to preparation and application of 2-aminopyrimidine heterocyclic compounds containing 4-acylamino phenoxy as shown in general formulas I and II, and pharmaceutically acceptable salts, hydrates, solvates and prodrugs of the compounds. Substituents X, R1 and R2 have meanings given in the specification. The compounds shown in the general formulas I and II have a strong effect ofinhibiting EGFR, EGFRT790M/L858R and EGFRT790M kinase; the compounds have very low inhibitory activity on human normal hepatocyte LO2. The invention also relates to application of the compounds and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of drugs for treating diseases caused by abnormal activation and high expression of EGFR kinase and positive mutation of T790M and L858R, particularly application in preparing medicines for treating and/or preventing cancers.