16233-51-5

Usage

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

Downstream Products

• 156943-14-5 1-<(2-benzoyloxy-1-benzoyloxymethyl)ethoxymethyl>-thieno<3,2-d>pyrimidine-2,4-dione 
• 153085-38-2 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thieno<3,2-d>pyrimidine-2,4-dione 
• 41102-25-4 7-bromo-2,4-dichloroimidazo[2,1-f][1,2,4]triazine 
• 153085-48-4 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methoxy thieno<3,2-d>pyrimidin-2-one 
• 153085-50-8 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-S-methyl thieno<3,2-d>pyrimidin-2-one 
• 153085-46-2 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-thioxo thieno<3,2-d>pyrimidin-2-one 
• 153085-52-0 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-S-ethyl thieno<3,2-d>pyrimidin-2-one 
• 16234-14-3 2,4-dichlorothieno[3,2-d]pyrimidine 
• 1308690-48-3 (S)-1-(4-(benzylamino)-7-ethynylthieno[3,2-d]pyrimidin-2-ylamino)propan-2-ol 
• 1308690-84-7 N-benzyl-2-chloro-7-vinylthieno[3,2-d]pyrimidin-4-amine 
• 1308690-57-4 3-(4-amino-2-(6-(4-ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide hydrochloride 
• 1308690-62-1 3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acid 
• 1308690-64-3 3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide 
• 1308689-70-4 3-(4-amino-2-(6-(4-ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide 

Relevant academic research and scientific papers

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 of 5-alkoxythieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine derivatives and evaluation of their anticonvulsant activities

This work concerns the design and synthesis of novel, substituted 5-alkoxythieno[2,3-e][1,2,4]triazolo[4,3-c ]pyrimidine derivatives 5a-p prepared from 3-amino-2-thiophenecarboxylic acid methyl ester. The final compounds were screened for their in vivo anticonvulsant activity using maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests. Neurotoxicity (NT) was tested using a rotarod test. The structure-anticonvulsant activity relationship analysis revealed that the most effective structural motif involves a substituted phenol, especially when substituted with a single chlorine, fluorine or trifluoromethyl group (at the meta-position), or two chlorine atoms. These molecules possessed high activity according to the MES and scPTZ models. Quantitative assessment of the compounds after intraperitoneal administration in mice showed that the most active compound was 5-[3-(trifluoromethyl)phenoxy]thieno[2,3-e] [1,2,4]triazolo[4,3-c]pyrimidine (5o) with ED50 values of 11.5 mg/kg (MES) and 58.9 mg/kg (scPTZ). Furthermore, compound 5o was more effective in the MES and scPTZ tests than the well-known anticonvulsant drugs carbamazepine and ethosuximide.

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.

Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines

The in vitro evaluation of thieno[3,2-d]pyrimidines identified halogenated compounds 1 and 2 with antiproliferative activity against three different cancer cell lines. A structure activity relationship study indicated the necessity of the chlorine at the C4-position for biological activity. The two most active compounds 1 and 2 were found to induce apoptosis in the leukemia L1210 cell line. Additionally, the compounds were screened against a variety of other microbial targets and as a result, selective activity against several fungi was also observed. The synthesis and preliminary biological results are reported herein.

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.

N-{2-[(2-chlorothieno[3,2-d]pyrimidin-4-yl)amino]ethyl}-3-methoxybenzamide: design, synthesis, crystal structure, antiproliferative activity, DFT, Hirshfeld surface analysis and molecular docking study

The compound N-{2-[(2-chlorothieno[3,2-d]pyrimidin-4-yl)amino]ethyl}-3-methoxybenzamide (8) was synthesized by the condensation of 3-methoxybenzoic acid (7) with N 1-(2-chlorothieno[3,2-d]pyrimidin-4-yl)ethane-1,2-diamine (6). This intermediate was prepared from methyl 3-aminothiophene-2-carboxylate (1) by the condensation with urea, chlorination with phosphorus oxychloride and then condensation with ethane-1,2-diamine. The crystal structure of the title compound was determined and the crystal of the title compound belongs to the tetragonal system, space group P4(3) with a = 9.4694(10) ?, b = 9.4694(10) ?, c = 18.886(3) ?, α = 90°, β = 90°, γ = 90°. The optimized geometric bond lengths and bond angles obtained by using density functional theory (DFT) have been compared with X-ray diffraction values. The calculated HOMO and LUMO energies showed the character of the title compound. The molecular electrostatic potential (MEP) surface map of the related molecule was investigated with theoretical calculations at the B3LYP/6-311 + G(d,p) levels. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. In addition, the title compound possesses marked inhibition against the proliferation of human colon cancer cell line HT-29 (IC50 = 1.76 μM), human lung adenocarcinoma cell line A549 (IC50 = 1.98 μM) and human gastric cancer cell line MKN45 (IC50 = 2.32 μM), displaying promising anticancer activitiy. The molecular docking studies revealed that the title compound may exhibit activity inhibiting PDB:3D15. Communicated by Ramaswamy H. Sarma.

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.

Synthesis and anticancer activities of thieno[3,2-d]pyrimidines as novel HDAC inhibitors

A series of thieno[3,2-d]pyrimidines bearing a hydroxamic acid moiety as novel HDAC inhibitors were designed and synthesized. The structures of the new synthesized compounds were confirmed using IR, 1H, 13C NMR spectrum. Compounds 11-13 showed potent inhibitory activities against HDACs with IC50 values at 0.38, 0.49 and 0.61 μM. Most of target compounds displayed strong anti-proliferative activity by a MTT assay on three human cancer cell lines including HCT-116, MCF-7 and HeLa. Compound 11, having potent inhibitory activities against HDACs, induced apoptosis and G2/M cell cycle arrest in HCT-116 cell line.

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.