18740-38-0

Basic information

• Product Name: 2,4-Dihydroxythieno[2,3-d]pyrimidine
• Synonyms: 2,4-Dihydroxythieno[2,3-d]pyrimidine;thieno[2,3-d]pyrimidine-2,4-diol;Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione;1H-Thieno[2,3-d]pyrimidine-2,4-dione
• CAS NO: 18740-38-0
• Molecular Formula: C₆H₄N₂O₂S
• Molecular Weight: 168.176
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 18740-38-0.mol

Chemical Properties

• Melting Point: 322 °C
• Appearance: /
• Density: 1.518g/cm³
• Refractive Index: 1.625
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 10.40±0.20(Predicted)
• CAS DataBase Reference: 2,4-Dihydroxythieno[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dihydroxythieno[2,3-d]pyrimidine(18740-38-0)
• EPA Substance Registry System: 2,4-Dihydroxythieno[2,3-d]pyrimidine(18740-38-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 18740-38-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dihydroxythieno[2,3-d]pyrimidine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a promising candidate for the development of new drugs with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,4-Dihydroxythieno[2,3-d]pyrimidine is used as a building block for the design and synthesis of novel bioactive molecules. Its structural diversity and potential for further functionalization make it an attractive starting point for the development of new drugs with improved pharmacological properties.
Used in Inhibitor Development:
2,4-Dihydroxythieno[2,3-d]pyrimidine is used as an inhibitor of dipeptidyl peptidase IV (DPP-IV), an enzyme involved in the regulation of glucose levels in the body. Inhibition of DPP-IV can help improve glycemic control in patients with type 2 diabetes, making this compound a potential therapeutic agent for the treatment of this condition.

InChI:InChI=1/C6H4N2O2S/c9-4-3-1-2-11-5(3)8-6(10)7-4/h1-2H,(H2,7,8,9,10)

Upstream product

• 18740-39-1 2,4-dichlorothieno[2,3-d]pyrimidine 
• 4651-81-4 Methyl 2-aminothiophene-3-carboxylate 
• 57-13-6 urea 
• 14080-51-4 2-aminothiophene-3-carboxamide 
• 56844-43-0 2-chlorothieno-[2,3-d]-pyrimidin-4(3H)-one 
• 51322-68-0 methyl 3-[(aminocarbonyl)amino]-2-thiophenecarboxylate 
• 917-61-3 sodium isocyanate 
• 4651-82-5 2-amino-3-cyanothiophene 
• 124-38-9 carbon dioxide 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 106666-44-8 methyl 2-ureidothiophene-3-carboxylate 

Downstream Products

• 18740-39-1 2,4-dichlorothieno[2,3-d]pyrimidine 
• 18740-44-8 thieno<2,3-d>pyrimidin-2,4(1H,3H)-dithione 
• 956388-12-8 2,4-dichloro-6-phenylfuro[3,2-d]pyrimidine 
• 1033744-45-4 4-(2-chloro-6-(3-(methylsulfonyl)phenyl)thieno[2,3-d ]pyrimidin-4-yl)morpholine 
• 1033735-40-8 5-(6-(3-(methylsulfonyl)phenyl)-4-morpholinothieno[2,3-d]-pyrimidin-2-yl)pyrimidin-2-amine 
• 63894-67-7 4-(2-chlorothiophen[2,3-d]pyrimidin-4-yl)morpholine 
• 1436866-44-2 2-[4-[(2-phenylthieno[2,3-d]pyrimidin-4-yl)amino]phenyl]acetic acid 
• 1436866-42-0 ethyl 2-[4-[(2-chlorothieno[2,3-d]pyrimidin-4-yl)amino]phenyl]acetate 
• 1436866-43-1 ethyl 2-[4-[(2-phenylthieno[2,3-d]pyrimidin-4-yl)amino]phenyl]acetate 
• 56844-18-9 2-chloro-4-phenyl-thieno[2,3-d]pyrimidine 

Relevant articles and documents

Ionic liquid promoted synthesis of heterocycle-fused pyrimidine-2,4(1H,3H)-diones utilising CO2

An efficient ionic liquid system was developed for the preparation of various heterocycle-fused pyrimidine-2, 4(1H,3H)-diones in moderate to excellent yields (52–95%). It was found that [HDBN+][TFE?], a simple and easily prepared ionic liquid, could act as both the solvent and reaction promoter, and that the reactions could be efficiently carried out at atmospheric pressures of CO2.

Design, synthesis, and biological evaluation of novel thienopyrimidine derivatives as PI3Kα inhibitors

Three series of novel thienopyrimidine derivatives 9a-l, 15a-l, and 18a-h were designed and synthesized, and their IC50 values against four cancer cell lines HepG-2, A549, PC-3, and MCF-7 were evaluated. Most compounds show moderate cytotoxicity against the tested cancer cell lines. The most promising compound 9a showed moderate activity with IC50 values of 12.32 ± 0.96, 11.30 ± 1.19, 14.69 ± 1.32, and 9.80 ± 0.93 μM, respectively. The inhibitory activities of compounds 9a and 15a against PI3Kα and mTOR kinase were further evaluated. Compound 9a exhibited PI3Kα kinase inhibitory activity with IC50 of 9.47 ± 0.63 μM. In addition, docking studies of compounds 9a and 15a were also investigated.

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands

Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.

Preparation method of heterocyclicpyrimidinedione compound

The invention discloses a preparation method of a heterocyclicpyrimidinedione compound and relates to the technology of medicinal chemistry. The preparation method comprises the following steps: 1) mixing an o-amino formonitrile heterocyclic compound and a catalyst to form a mixture, wherein the catalyst is [HDBN][TFE]; 2) in a CO2 environment, heating the mixture and reacting; 3) when the temperature is reduced to room temperature, adjusting the pH value to neutrality, and extracting, separating and collecting the an organic phase; drying, filtering and then vaporizing; performing column chromatography separation to obtain the heterocyclicpyrimidinedione compound. The preparation method disclosed by the invention has the advantages of low cost, environmental friendliness, simple preparation process and wide application range of substrate.

Heterocyclic-pyrimindine or pyrazine compound containing biarylamide structure and application thereof

The invention discloses a heterocyclic-pyrimindine or pyrazine compound containing a biarylamide structure. The heterocyclic-pyrimindine or pyrazine compound is as shown in a general formula I or II, wherein the general formula I and the general formula II are shown in the description. The heterocyclic-pyrimindine or pyrazine compound containing the biarylamide structure, and pharmaceutically acceptable salts, hydrates or solvates thereof are used as active components, and are mixed with a pharmaceutically acceptable carrier or excipient to prepare a composition; and the composition is prepared into clinically acceptable preparations. The compound provided by the invention can be used for treating and/or preventing proliferative diseases, and treating and/or preventing prostate cancer, lung cancer and cervical cancer.

Heteroarylpyrimindinedione derivative and use thereof

The invention provides a heteroarylpyrimindinedione derivative and use thereof. The heteroarylpyrimindinedione derivative comprises a compound with a structure shown as general formula I, and a pharmaceutically acceptable salt or hydrate thereof. The derivative is obtained by chemical synthesis, and pharmacological experiments prove that the active ligand with cannabinoid type II receptor CB2 can be used for preparation of drugs for prevention and mitigation of CB2 receptor-mediated diseases, and the drug is cannabinoid CB2 receptor agonist's agonist, partial agonist, inverse agonist or antagonist. And the general structural formula I is shown as the specification.

The structure containing [...] of thienopyrimidines preparation and application

The invention discloses a thienopyrimidine compound containing a chromone hydrazone structure, a geometrical isomer of the compound, pharmaceutically acceptable salts, hydrates, solvates or prodrugs of the compound, as well as application of the compound to preparation of medicines for treating and/or preventing hyperplastic diseases, application of the compound to preparation of medicines for treating and/or preventing cancers and application of the compound to preparation of medicines for treating and/or preventing lung cancers, liver cancers, gastric cancers, colon cancers and breast cancers.

Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors

Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.

Identification of 2,4-diamino-6,7-dimethoxyquinoline derivatives as G9a inhibitors

G9a is a histone lysine methyltransferase (HKMT) involved in epigenetic regulation via the installation of histone methylation marks. 6,7-Dimethoxyquinazoline analogues, such as BIX-01294, are established as potent, substrate competitive inhibitors of G9a. With an objective to identify novel chemotypes for substrate competitive inhibitors of G9a, we have designed and synthesised a range of heterocyclic scaffolds, and investigated their ability to inhibit G9a. These studies have led to improved understanding of the key pharmacophoric features of BIX-01294 and the identification of a new core quinoline inhibitory scaffold, which retains excellent potency and high selectivity. Molecular docking was carried out to explain the observed in vitro data. This journal is

The highly potent and selective dipeptidyl peptidase IV inhibitors bearing a thienopyrimidine scaffold effectively treat type 2 diabetes

New dipeptidyl peptidase IV inhibitors were designed based on Alogliptin using a scaffold-hopping strategy. All of the compounds constructed on a thienopyrimidine scaffold demonstrated good inhibition and selectivity for DPP-IV. Compound 10d exhibited subnanomolar (IC50 = 0.33 nM) DPP-IV inhibitory activity, good in vivo efficacy and an acceptable pharmacokinetic profile. A pharmacokinetic-driven optimization of 10d may lead to a new class of clinical candidate DPP-IV inhibitors.