16233-51-5

Basic information

• Product Name: 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione
• Synonyms: 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione;hieno[3,2-d]pyrimidine-2,4-diol;thieno[3,2-d]pyrimidine-2,4-diol;Thieno[3,2-d]pyrimidine2,4(1H,3H)-dione;1H-Thieno[3,2-d]pyrimidine-2,4-dione;2,4-Dihydroxythieno[3,2-d]pyrimidine ,97%;1H-Thieno[3,2-d][1,3]oxazine-2,4-dione;2-d]pyriMidine-2
• CAS NO: 16233-51-5
• Molecular Formula: C₆H₄N₂O₂S
• Molecular Weight: 168.17
• Product Categories: Heterocycles;API intermediates;Heterocycle-Pyrimidine series
• Mol File: 16233-51-5.mol
• Article Data: 85

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 274.804oC at 760 mmHg
• Flash Point: 119.997oC
• Appearance: /
• Density: 1.518 g/cm³
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.715
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.40±0.20(Predicted)
• CAS DataBase Reference: 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione(16233-51-5)
• EPA Substance Registry System: 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione(16233-51-5)

Safety Data

• Statements: 20/21/22
• Safety Statements: 24/25-36/37
• Hazardous Substances Data: 16233-51-5(Hazardous Substances Data)

Usage

Description

1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione is a chemical compound belonging to the class of thienopyrimidines. It is characterized by its grey solid appearance and possesses unique chemical properties that make it suitable for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione is used as a therapeutic agent for the development of inhibitors targeting dipeptidyl peptidase IV (DPP-IV) and protein kinase D (PKD), which are serine/threonine kinases. These inhibitors play a crucial role in the treatment of various diseases, including type 2 diabetes and certain cancers.
Additionally, 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione is utilized in the synthesis of antagonists for the human adenosine A2B receptor. These antagonists have potential applications in the treatment of asthma, chronic obstructive pulmonary disease (COPD), and other inflammatory conditions.
Used in Chemical Synthesis:
1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione serves as a key intermediate in the synthesis of various complex organic molecules. Its unique chemical structure allows for further functionalization and modification, making it a valuable building block in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C6H2Cl2N2S/c7-5-4-3(1-2-11-4)9-6(8)10-5/h1-2H

Upstream product

• 590-28-3 potassium cyanate 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 917-61-3 sodium isocyanate 
• 51322-68-0 methyl 3-[(aminocarbonyl)amino]-2-thiophenecarboxylate 
• 55341-87-2 3-aminothiophene-2-carboxylic acid 
• 57-13-6 urea 
• 31895-77-9 2-thioxo-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 1132690-58-4 3-amino-1H-thieno[3,2-d]pyrimidine-2,4-dione 
• 147123-47-5 3-aminothiophene-2-carboxamide 
• 137844-98-5 3-aminothiophene-2-carbohydrazide 
• 147123-50-0 thieno<3,2-d>-1,2,3-triazin-4(3H)-one 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 1259978-29-4 2-methoxythieno[3,2-d]pyrimidine 

Relevant articles and documents

Synthesis and antibacterial activity of thienopyrimidine amide derivatives

Thienopyrimidine amide derivatives are important class of organic compounds and show wide range of biological activity. Hence the researchers are paying more attention towards the synthesis of these compounds. A series of thienopyrimidine amide derivatives (13a-m) were synthesized. The newly synthesized amide derivatives (13a-m) were characterized by 1H NMR, 13C NMR, Mass and IR spectral data. Further these compounds were also evaluated for their antibacterial activity.

Synthesis, crystal and antiproliferative activity of 2-[2-(2-fluorobenzylidene) hydrazinyl]-4-(1-methyl-1H-indol-3-yl)thieno[3,2-d]pyrimidine

The title compound 2-[2-(2-fluorobenzylidene)hydrazinyl]-4-(1-methyl-1H-indol-3-yl) thieno[3,2-d]pyrimidine (C22H16FN5S) was prepared and its structure was confirmed by IR, 1H NMR, MS, elemental analyses and X-ray diffraction. The crystal of the title compound belongs to the monoclinic system, space group P21/c with a = 14.4546(17) ?, b = 17.0895(19) ?, c = 17.9621(15) ?, α = 90°, β = 122.717(6), γ = 90°, V = 3733.1(7) ?3, Z = 4, and R = 0.0412 for 4816 observed reflections with I > 2σ(I). In addition, the compound possesses distinct effective inhibition on the proliferation of HT-29, A549 and MKN45 cell lines.

Synthesis and antibacterial activity of novel 4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}-benzohydrazide derivatives

A series of novel 4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}benzohydrazide derivatives were synthesized and evaluated for their antibacterial activity. Most of the compounds demonstrated high activity towards Escherichia coli, Pseudomonas, Staphylococcus aureus, and Bacillus. Structures of all synthesized compounds were confirmed by spectral analysis.

Antagonists of the human adenosine A2A receptor. Part 2: Design and synthesis of 4-arylthieno[3,2-d]pyrimidine derivatives

We describe herein the discovery and development of a series of 4-arylthieno[3,2-d]pyrimidines which are potent adenosine A2A receptor antagonists. These novel compounds show high degrees of selectivity against the human A1, A2B and A3 receptor sub-types. Moreover, a number of these compounds show promising activity in vivo, suggesting potential utility in the treatment of Parkinson's disease.

Discovery of novel and potent PARP/PI3K dual inhibitors for the treatment of cancer

PARP inhibitors have achieved great success in cancers with BRCA mutations, but only a small portion of patients carry BRCA mutations, which results in their narrow indication spectrum. Recently, emerging evidence has demonstrated that combinations of PARP and PI3K inhibitors could evoke unanticipated synergistic effects in various cancers, even including BRCA-proficient ones. In this work, a series of PARP/PI3K dual inhibitors were designed, synthesized, and evaluated for their biological activities. It was found that compounds 9a and 23a exhibited excellent inhibitory activities against PARP-1 (9a: IC50 = 1.57 nM, 23a: IC50 = 0.91 nM) and PI3Kα (9a: IC50 = 2.0 nM, 23a: IC50 = 1.5 nM), and showed promising antiproliferative activities against both BRCA-deficient (HCT-116, HCC-1937) and BRCA-proficient (SW620, MDA-MB-231/468) tumor cells. 9a and 23a also exhibited considerable in vivo antitumor efficacy in an MDA-MB-468 xenograft mouse model, with TGI values of 56.39% and 48.77%, respectively. Additionally, 23a possessed promising profiles including high kinase selectivity and low cardiotoxicity. Overall, this work indicates 9a and 23a might be potential PARP/PI3K dual inhibitors for cancer therapy and deserve further research.

PARP-1/PI3K double-target inhibitor or pharmaceutically acceptable salt thereof, preparation method and application thereof

The invention discloses a PARP-1/PI3K double-target inhibitor or a pharmaceutically acceptable salt thereof, a preparation method and application thereof. According to the invention, the single active component can play a dual inhibition role on PARP-1 and PI3K, so that the dosage is reduced, the treatment effect is improved, and the toxic and side effects are reduced; and the dual inhibition effect on PARP-1 and PI3K is significant, the IC50 value of each target does not exceed 1.0 [mu]M, and the drug using the PARP-1/PI3K double-target inhibitor as the active component can be used for treating a variety of cancers or tumors related to PARP-1 and/or PI3K.