19819-18-2

Upstream product

• 93-89-0 benzoic acid ethyl ester 
• 4815-28-5 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 100-47-0 benzonitrile 
• 100-52-7 benzaldehyde 
• 108-94-1 cyclohexanone 
• 52535-73-6 4,5,6,7-tetrahydrobenzothiophene-2-benzoylamino-3-carboxylic acid 
• 73696-35-2 5,6,7,8-tetrahydro-2-phenyl-4H-benzo<4,5->thieno<2,3-d><3,1>-oxazin-4-one 
• 5936-58-3 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 825-60-5 benzimidic acid ethyl ester 
• 19819-17-1 2-benzamido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 35149-32-7 4-chloro-2-phenyl-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 60557-11-1 N,2-diphenyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine 
• 83548-65-6 (2-Phenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-hydrazine 
• 83548-72-5 4-Phenyl-7,8,9,10-tetrahydro-6-thia-1,2,3,3a,5-pentaaza-cyclopenta[c]fluorene 
• 947328-96-3 2-phenyl-4-[(3-hydroxy)propyl]amino-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidine 
• 1225504-81-3 2-phenyl-4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine 
• 1225504-83-5 2-phenyl-3-prop-2-yn-1-yl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one 
• 60557-12-2 ethyl-phenyl-(2-phenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine 
• 60557-14-4 4-(4-methyl-piperazin-1-yl)-2-phenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine 
• 60557-10-0 dibutyl-(2-phenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine 
• 60557-13-3 4-morpholino-2-phenyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine 
• 35149-35-0 4-methanesulfinylmethyl-2-phenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine 
• 35149-33-8 2,4-diphenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine 
• 35149-36-1 2-phenyl-4-methoxy-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of new thieno[2,3-d] pyrimidine derivatives as targeted therapy for PI3K with molecular modelling study

Cancer is one of the most aggressive diseases characterised by abnormal growth and uncontrolled cell division. PI3K is a lipid kinase involved in cancer progression which makes it fruitful target for cancer control. 28 new morpholine based thieno[2,3-d] p

Discovery of Thieno[2,3- d]pyrimidine-Based Hydroxamic Acid Derivatives as Bromodomain-Containing Protein 4/Histone Deacetylase Dual Inhibitors Induce Autophagic Cell Death in Colorectal Carcinoma Cells

Bromodomain-containing protein 4 (BRD4) and histone deacetylases (HDAC) are both attractive epigenetic targets in cancer and other chronic diseases. Based on the integrated fragment-based drug design, synthesis, and in vitro and in vivo evaluations, a series of novel thieno[2,3-d]pyrimidine-based hydroxamic acid derivatives are discovered as selective BRD4-HDAC dual inhibitors. Compound 17c is the most potent inhibitor for BRD4 and HDAC with IC50 values at nanomolar levels, as well as the expression level of c-Myc, and increases the acetylation of histone H3. Moreover, 17c presents inhibitory effects on the proliferation of colorectal carcinoma (CRC) cells via inducing autophagic cell death. It also has a good pharmacokinetic profile in rats and oral bioavailability of 40.5%. In the HCT-116 xenograft in vivo models, 17c displays potent inhibitory efficiency on tumor growth by inducing autophagic cell death and suppressing IL6-JAK-STAT signaling pathways. Our results suggest that the BRD4-HDAC dual inhibition might be an attractive therapeutic strategy for CRC.

ZnO-CeO2 nanocomposite: Efficient catalyst for the preparation of thieno[2,3-d]pyrimidin-4(3H)-one derivatives

The Zinc oxide-cerium oxide (ZnO-CeO2) nanocomposite was prepared by a coprecipitation method and characterized by X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), and particle size distribution analysis. The XRD p

Thienopyrimidine derivatives exert their anticancer efficacy via apoptosis induction, oxidative stress and mitotic catastrophe

In this study, a series of 13 structural variants of thieno[2,3d]pyrimidine derivatives (6a-6m) were synthesized and screened for cytotoxicity in a panel of colorectal, ovarian, and brain cancer cell lines. The selectivity of the compounds was assessed by

Design, synthesis, and biological activity of tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine derivatives as anti-inflammatory agents

We designed and synthesized 26 prototype compounds and studied their anti-inflammatory activity and underlying molecular mechanisms. The inhibitory effects of the compounds on the production of nitric oxide (NO), cytokines, inflammatory-related proteins, and mRNAs in lipopolysaccharide (LPS)-stimulated macrophages were determined by the Griess assay, Enzyme linked immunosorbent assay (ELISA), Western blot analysis, and Reverse transcription-Polymerase Chain Reaction (RT-PCR), respectively. Our results indicated that treatment with A2, A6 and B7 significantly inhibited the secretion of NO and inflammatory cytokines in RAW264.7 cells without demonstrable cytotoxicity. It was also found that A2, A6 and B7 strongly suppressed the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase enzyme COX-2, and prevented nuclear translocation of nuclear factor κB (NF-κB) p65 by inhibiting the degradation of p50 and IκBα. Furthermore, the phosphorylation of mitogen-activated protein kinase (MAPKs) in LPS-stimulated RAW264.7 cells was significantly inhibited by A2, A6 and B7. These findings suggest that A2, A6 and B7 may operate as an effective anti-inflammatory agent through inhibiting the activation of NF-κB and MAPK signaling pathways in macrophages. Moreover, rat paw swelling experiments showed that these compounds possess anti-inflammatory activity in vivo, with compound A6 exhibiting similar activities to the reference drug Indomethacin.

Discovery of a Small-Molecule Bromodomain-Containing Protein 4 (BRD4) Inhibitor That Induces AMP-Activated Protein Kinase-Modulated Autophagy-Associated Cell Death in Breast Cancer

Upon the basis of The Cancer Genome Atlas (TCGA) data set, we identified that several autophagy-related proteins such as AMP-activated protein kinase (AMPK) were remarkably downregulated in breast cancer. Combined with coimmunoprecipitation assay, we demonstrated that BRD4 might interact with AMPK. After analyses of the pharmacophore and WPF interaction optimization, we designed a small-molecule inhibitor of BRD4, 9f (FL-411) which was validated by cocrystal structure with BD1 of BRD4. Subsequently, 9f was discovered to induce ATG5-dependent autophagy-associated cell death (ACD) by blocking BRD4-AMPK interaction and thus activating AMPK-mTOR-ULK1-modulated autophagic pathway in breast cancer cells. Interestingly, the iTRAQ-based proteomics analyses revealed that 9f induced ACD pathways involved in HMGB1, VDAC1/2, and eEF2. Moreover, 9f displayed a therapeutic potential on both breast cancer xenograft mouse and zebrafish models. Together, these results demonstrate that a novel small-molecule inhibitor of BRD4 induces BRD4-AMPK-modulated ACD in breast cancer, which may provide a candidate drug for future cancer therapy.

Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis

Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacterium tuberculosis (MTB), enzymatic screening and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-ethyl-N-phenethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine (5c) was found to be the most active compound against non-replicative MTB with 2.7 log reduction of bacteria at 10?μg/mL and was more potent than isoniazid (1.2 log reduction) and rifampicin (2.0 log reduction) at same dose level. Compound 5c also showed activity against MTB alanine dehydrogenase enzyme with IC50of 1.82?±?0.42?μM and showed 25% cytotoxicity against RAW 264.7 cell line at 50?μg/mL.

Synthesis of some new tetrahydrobenzo[b] thiophene derivatives and tetrahydrobenzo-thienopyrimidine derivatives under microwave irradiation

2-Phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]oxazin-4-one (4) was reacted with either aliphatic or aromatic primary amines such as benzylamine, cyclohexylamine, p-toluidine, and=or p-anisidine to give carboxamide derivatives 5a-d, respectively. A

Synthesis and theoretical studies on energetics of novel N- and O- perfluoroalkyl triazole tagged thienopyrimidines - Their potential as adenosine receptor ligands

A series of novel N- and O- perfluoroalkyl triazole tagged thienopyrimidines 6a-c and 7a-d was synthesized in two steps from thienopyrimidin-4-ones 2 through O- and N-propargylated regioisomers 3a-i and 4a-i respectively. Compound 2 was reacted with propargyl bromide to form O- and N-propargylated regioisomers 3 and 4 in definite proportions. Each regioisomer was separated and independently subjected to [3?+?2] cycloaddition using perfluoroalkyl azides through Click reaction under Sharpless conditions and obtained exclusively anti product in each case. The formation of two regioisomers in the first step and single anti addition product in the next step could be explained based on computational studies carried out at B3LYP/6-31G(d) level of theory. Results of Fukui function indices at the reactive centers are in accordance with the observations. On evaluation of the synthesized molecules for their binding affinities towards adenosine receptors, 4d and 4f were found to be selective to A1 over A2A receptors.

Three possible products from the reactions of Gewald's amide with aromatic aldehydes

(Chemical Equation Presented) Transformations of 2-amino-4,5,6,7- tetrahydrobenzo[b]thiophene-3-carboxamide (Gewald's amide) in the reactions with aromatic aldehydes were studied. Efficient methods for synthesis of three possible types of products: 2-aryl