40106-31-8

Usage

InChI:InChI=1/C11H12N2OS/c14-10-9-7-4-2-1-3-5-8(7)15-11(9)13-6-12-10/h6H,1-5H2,(H,12,13,14)

Upstream product

• 40106-12-5 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide 
• 122-51-0 orthoformic acid triethyl ester 
• 40106-58-9 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3- d]pyrimidine 
• 40106-13-6 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid ethyl ester 
• 3473-63-0 formamidine acetic acid 
• 77287-34-4 formamide 
• 350997-73-8 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid 
• 502-42-1 cycloheptanone 
• 64-18-6 formic acid 
• 23917-22-8 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonitrile 

Downstream Products

• 1345512-69-7 N'-[(3-hydroxyphenyl)methylene]-(4-oxo-6,7,8,9-tetrahydro-5H-cyclohepta [4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone 
• 1345512-71-1 N'-[(4-hydroxyphenyl)methylene]-(4-oxo-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone 
• 379256-89-0 4-(4-phenylpiperazine-1-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidine 
• 924121-98-2 4-(4-methylpiperazin-1-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Cycloalkyl thienopyrimidinone compounds as well as preparation method and application thereof

The invention relates to a parent nucleus compound containing cycloalkyl[4,5]thieno[2,3-d]pyrimidin-4 (3H)-one, and the parent nucleus compound has the following structure shown in the specification,wherein R1, X, m and n are defined in the specification.

Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor

We recently described a structurally novel series of negative allosteric modulators (NAMs) of the dopamine D2 receptor (D2R) based on thieno[2,3-d]pyrimidine 1, showing it can be structurally simplified to reveal low molecular weight, fragment-like NAMs that retain robust negative cooperativity, such as 3. Herein, we report the synthesis and functional profiling of analogues of 3, placing specific emphasis on examining secondary and tertiary amino substituents at the 4-position, combined with a range of substituents at the 5/6-positions (e.g. aromatic/aliphatic carbocycles). We identify analogues with diverse pharmacology at the D2R including NAMs with sub-μM affinity (9h) and, surprisingly, low efficacy partial agonists (9d and 9i).

Identification of 4-methoxythieno[2,3-d]pyrimidines as FGFR1 inhibitors

Aim. To identify novel FGFR1 inhibitors using virtual screening approach. Methods. We used methods of organic synthesis, molecular docking via the Autodock 4.2.6 program package and in vitro biochemical tests with γ-32P. Results. In vitro experiments showed that 9 of 23 tested compounds possess inhibitory activity against FGFR1 with IC50 values in the range from 0.9 to 5.6 μM. Conclusions. Nine FGFR1 inhibitors were developed. The mode of compounds binding with the ATP-acceptor site was determined using molecular docking methods and the dependence of the compounds’ activity on the substituents R1, R4 and R5 was evaluated.

Novel thienopyrimidine derivatives as dual EGFR and VEGFR-2 inhibitors: design, synthesis, anticancer activity and effect on cell cycle profile

Aim: Design and synthesis of thienopyrimidine derivatives as dual EGFR and VEGFR-2 inhibitors.Material and methods: A series of novel 6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidine derivatives with different substituents on C-4 position was synthesized and evaluated for their anticancer activity against MCF-7 cell line. EGFR, VEGFR-2 inhibitory assay, the cell cycle analysis and apoptosis induction ability of the most potent compound 5f were evaluated.Results: Most of the compounds showed moderate to significant anticancer activity. Compound 5f exhibited the most potent anticancer activity being 1.73- and 4.64-folds more potent than erlotinib and doxorubicin, respectively. Compound 5f showed potent EGFR inhibitory activity being 1.18-folds more potent than reference standard erlotinib and it also showed good VEGFR-2 inhibitory activity at the micromolar level with IC50 value 1.23?μM. Compound 5f caused induction of cell cycle arrest at G2/M phase and accumulation of cells in pre-G1 phase. Compound 5f induced cellular apoptosis.

Structure based design of selective SHP2 inhibitors by De novo design, synthesis and biological evaluation

SHP2 phosphatase, encoded by the PTPN11 gene, is a non-receptor PTP, which plays an important role in growth factor, cytokine, integrin, hormone signaling pathways, and regulates cellular responses, such as proliferation, differentiation, adhesion migrati

Design and synthesis of novel annulated thienopyrimidines as phosphodiesterase 5 (PDE5) inhibitors

Novel cycloalkene-fused thienopyrimidine analogues with enhanced phosphodiesterase 5 (PDE5) inhibitory properties are presented. The structure of the reported scaffold was modulated through variation of the terminal cycloalkene ring size, as well as by va

A facile microwave-assisted synthesis of some fused pyrimidine derivatives

The highly accelerated synthesis of thienopyrimidinones, theino- pyrimidines, thioxotheinopyrimidinones and a thienotriazolopyrimidinone derivatives under microwave irradiation is reported. Compared to conventional conditions, microwaves method offered se

C-C (alkynylation) vs C-O (ether) bond formation under Pd/C-Cu catalysis: Synthesis and pharmacological evaluation of 4-alkynylthieno[2,3-d]pyrimidines

The Pd/C-CuI-PPh3 catalytic system facilitated C-C bond formation between 4-chlorothieno[2,3-d]pyrimidines and terminal alkynes in methanol with high selectivity without generating any significant side products arising from C-O bond formation b

Synthesis and anti-tumor activities of N′-benzylidene-2-(4- oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone derivatives

A compound with a cyclic thienopyrimidine moiety and an aceto-hydrazone moiety in its chemical structure was discovered in a cell-based screening to have noticeable cytotoxicity on several tumor cell lines. A total of 38 derivatives of this compound were

Identification of 5,6-substituted 4-aminothieno[2,3-d]pyrimidines as LIMK1 inhibitors

4-Aminobenzothieno[3,2-d]pyrimidines were previously identified in a high throughput screening campaign as LIMK1 inhibitors. Scaffold reversal led to the identification of a series of simple 5,6-substituted 4-aminothieno[2,3-d] pyrimidines with low micromolar inhibition of LIMK1.