16234-15-4

Basic information

• Product Name: 2-Chloro-4-(morpholin-4-yl)thieno[3,2-d]pyrimidine
• Synonyms: 2-Chloro-4-(morpholin-4-yl)thieno[3,2-d]pyrimidine;2-Chloro-4-(4-morpholinyl)thieno[3,2-d]pyrimidine;4-(2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine;2-chloro-4-(4-Morpholinyl)-;2-chloro-4-Morpholinothieno[3,2-d]pyriMidine;Thieno[3,2-d]pyriMidine, 2-chloro-4-(4-Morpholinyl)-;2-Chloro-4-(morpholin-4-yl)thieno[3,2-d]pyrimidine-4;4-(2-Chlorothieno[3,2-d]pyrimidin-4-yl)
• CAS NO: 16234-15-4
• Molecular Formula: C₁₀H₁₀ClN₃OS
• Molecular Weight: 255.72
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 16234-15-4.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 393.748 °C at 760 mmHg
• Flash Point: 191.932 °C
• Appearance: /
• Density: 1.463
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.82±0.40(Predicted)
• CAS DataBase Reference: 2-Chloro-4-(morpholin-4-yl)thieno[3,2-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-(morpholin-4-yl)thieno[3,2-d]pyrimidine(16234-15-4)
• EPA Substance Registry System: 2-Chloro-4-(morpholin-4-yl)thieno[3,2-d]pyrimidine(16234-15-4)

Safety Data

• Hazardous Substances Data: 16234-15-4(Hazardous Substances Data)

Usage

General Description

2-Chloro-4-(morpholin-4-yl)thieno[3,2-d]pyrimidine is a complex organic compound that includes chlorine, nitrogen, and sulfur in a pyrimidine and thieno structure. Its formula is C9H8ClN3OS. As a compound, it is used in various research and development processes, particularly within the pharmaceutical industry. It potentially serves as an intermediate in the synthesis of certain drugs or chemical compounds. It's a relatively specialized chemical and typically requires specific handling and storage conditions due to its reactivity. MIT undergraduates don't generally use this chemical in their standard laboratory procedures.

InChI:InChI=1/C10H10ClN3OS/c11-10-12-7-1-6-16-8(7)9(13-10)14-2-4-15-5-3-14/h1,6H,2-5H2

Upstream product

• 110-91-8 morpholine 
• 16234-14-3 2,4-dichlorothieno[3,2-d]pyrimidine 
• 16233-51-5 1H-thieno[3,2-d]pyrimidine-2,4-dione 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 16233-51-5 2,4-dihydroxythieno[3,2-d]pyrimidine 

Downstream Products

• 885618-31-5 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde 
• 885698-97-5 2-chloro-4-morpholinylthiophene[3,2-d]pyrimidine-6-methanol 
• 885698-98-6 4-(6-(bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine 
• 885675-66-1 4-(2-chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]-pyrimidin-4-yl)morpholine 
• 1235450-27-7 Ethyl 2-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methylamino)pyrimidine-5-carboxylate 
• 1235450-94-8 methyl 2-(((2-(4-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-97-1 methyl 2-(((2-(3-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235451-07-6 ethyl 2-(((2-(4-aminophenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-95-9 ethyl 2-(((2-(4-(acetamidomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidine-6-yl)Methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-96-0 2-(((2-(4-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylic acid 
• 1235450-98-2 ethyl 2-(((2-(3-(acetamidomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidine-6-yl)Methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-99-3 2-(((2-(3-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylic acid 
• 1235451-08-7 ethyl 2-(((2-(4-acetamidophenyl)-4-morpholinothieno-[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1394047-62-1 (E)-3-((3-((2-(6-((4-(methylsulfonyl)piperazin-1-yl)-methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)hydrazono)-methyl)-1H-indol-1-yl)methyl)benzonitrile 

Relevant articles and documents

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.

Design, synthesis and biological evaluation of thieno[3,2-d]pyrimidine derivatives containing aroyl hydrazone or aryl hydrazide moieties for PI3K and mTOR dual inhibition

Recently, PI3K and mTOR have been regarded as promising targets for cancer treatment. Herein, we designed and synthesized four series of novel thieno[3,2-d]pyrimidine derivatives that containing aroyl hydrazone or aryl hydrazide moieties. These derivatives act as PI3K/mTOR dual inhibitors, suggesting that they can be used as cancer therapeutic agents. All compounds were tested for anti-proliferative activity against four cancer cell lines. The structure-activity relationship (SAR) studies were conducted by varying the moieties at the C-6 and C-2 positions of the thieno[3,2-d]pyrimidine core. It indicated that aryl hydrazide at C-6 position and 2-aminopyrimidine at C-2 position are optimal fragments. Compound 18b showed the most potent in vitro activity (PI3Kα IC50 = 0.46 nM, mTOR IC50 = 12 nM), as well as good inhibition against PC-3 (human prostate cancer), HCT-116 (human colorectal cancer), A549 (human lung adenocarcinoma) and MDA-MB-231 (human breast cancer) cell lines. Furthermore, Annexin-V and propidium iodide (PI) double staining confirmed that 18b induces apoptosis in cytotoxic HCT-116 cells. Moreover, the influence of 18b on cell cycle distribution was assessed on the HCT-116 cell line, and a cell cycle arrest was observed at the G1/S phases.