23917-22-8

Basic information

• Product Name: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBONITRILE
• Synonyms: 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonitrile(SALTDATA: FREE);2-Amino-3-cyano-4,5-pentamethylene thiophene;2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiophene-3-carbonitrile
• CAS NO: 23917-22-8
• Molecular Formula: C₁₀H₁₂N₂S
• Molecular Weight: 192.28
• Mol File: 23917-22-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: 115-117 °C(Solv: ethanol (64-17-5))
• Boiling Point: 406.4 °C at 760 mmHg
• Flash Point: 199.6 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 8.15E-07mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -0.09±0.20(Predicted)
• CAS DataBase Reference: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBONITRILE(23917-22-8)
• EPA Substance Registry System: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBONITRILE(23917-22-8)

Safety Data

• Hazardous Substances Data: 23917-22-8(Hazardous Substances Data)

Usage

General Description

2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBONITRILE is a chemical compound with the molecular formula C9H10N2S. It is a heterocyclic compound containing a thiophene ring and a cyano group, commonly used in the pharmaceutical industry as a building block for the synthesis of various pharmaceutical drugs. 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBONITRILE has potential applications in drug discovery and development due to its pharmacological properties. It is also used as a starting material in organic synthesis, particularly in the preparation of heterocyclic compounds. The unique structure and properties of 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBONITRILE make it a valuable compound in the field of medicinal and organic chemistry.

InChI:InChI=1/C10H12N2S/c11-6-8-7-4-2-1-3-5-9(7)13-10(8)12/h1-5,12H2

Upstream product

• 2235-08-7 Propargyl nitrile 
• 502-42-1 cycloheptanone 
• 10394-94-2 cycloheptylidene-malononitrile 
• 109-77-3 malononitrile 

Downstream Products

• 384847-18-1 2,3,4,7,8,9,10,11-octahydro-1H-cyclohepta[4,5]thieno[2,3-b]quinolin-12-amine 
• 515149-95-8 N-(3-Cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)-2-iodobenzamide 
• 1240504-54-4 2-[(1-benzyl-5-oxo-2-phenyl-4-trifluoromethyl-4,5-dihydroimidazol-4-yl)amino]-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonitrile 
• 1243985-29-6 2-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]thieno[2,3-d]pyrimidin-4-amine 
• 1243985-28-5 2-p-tolyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]thieno[2,3-d]pyrimidin-4-amine 
• 1243985-27-4 2-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-amine 
• 1243985-30-9 2-(2-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]thieno[2,3-d]pyrimidin-4-amine 
• 261781-18-4 2-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]thieno[2,3-d]pyrimidin-4-amine 
• 40106-59-0 1-hydrazino cyclohepta(b)thieno[2,3-d]pyrimidine 
• 40106-58-9 4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3- d]pyrimidine 
• 380907-31-3 1-(3,5-dimethyl-1H-pyrazol-1-yl)cyclohepta(b)thieno[2,3-d]pyrimidine 
• 309277-28-9 2-amino-1-(3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]thien-2-yl)-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 

Relevant articles and documents

Calcined Mg-Al hydrotalcite as a heterogeneous base catalyst for gewald aminothiophene synthesis

Calcined Mg-Al hydrotalcite (Mg/Al=4) has been conveniently employed as a heterogeneous base catalyst in the synthesis of 2-amino-3-cyanothiophenes adopting a one pot Gewald aminothiophene methodology.

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.

Convenient synthesis of 2-aminothiophene derivatives by acceleration of gewald reaction under ultrasonic aqueous conditions

Under ultrasound irradiation and in the presence of H2O/Et 2NH, ethyl cyanoacetate or malononitrile can combine with-methylene carbonyl compounds and elemental sulfur to efficiently yield 2-aminothiophene derivatives within a few minutes. Products are easily obtained by simple filtration because of their spontaneous precipitation in the reaction mixtures. Copyright Taylor & Francis Group, LLC.

New thiophene–acridine compounds: Synthesis, antileishmanial activity, DNA binding, chemometric, and molecular docking studies

In this study, we synthesized eight new compounds containing the 2-amino-cycloalkyl[b]thiophene and acridine moieties (ACT01 and ACS01-ACS07). None tested compounds presented human erythrocyte cytotoxicity. The new compounds presented antipromastigote activity, where ACS01 and ACS02 derivatives presented significant antileishmanial activity, with better performance than the reference drugs (tri and pentavalent antimonials), with respective IC50 values of 9.60?±?3.19 and 10.95?±?3.96?μm. Additionally, these two derivatives were effective against antimony-resistant Leishmania (Leishmania) amazonensis strains. In addition, binding and fragmentation DNA assays were performed. It was observed that the antileishmanial activity of ACS01 is not associated with DNA fragmentation of the promastigote forms. However, it interacted with DNA with a binding constant of 104?m?1. In partial least-squares studies, it was observed that the most active compounds (ACS01 and ACS02) showed lower values of amphiphilic moment descriptor, but there was a correlation between the lipophilicity of the molecules and antileishmanial activity. Furthermore, the docking molecular studies showed interactions between thiophene–acridine derivatives and the active site of pyruvate kinase enzyme with the major contribution of asparagine 152 residue for the interaction with thiophene moiety. Thus, the results suggested that the new thiophene–acridine derivatives are promising molecules as potential drug candidates.

Decomposition of Thiopyrans to Thiophenes Under Electron Impact

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Synthesis and biological evaluation of novel hybrid compounds derived from gallic acid and the 2-aminothiophene derivatives

Abstract: Gallic acid (GA) and its benzamide derivatives have a wide variety of biological activities, such as antimicrobial, antioxidant, anticancer. In this study, we have reported the synthesis of some new hybrid compounds comprised of the 2-aminothiophene and GA moieties and evaluation of their cytotoxic activities against HeLa (cervical cancer), HCT116 (human colon cancer), and FT (fibroblast) cell lines as well as antimicrobial activities against some Gram-positive and Gram-negative bacteria. The reaction of some 2-aminothiophene derivatives (previously prepared from the Gewald reaction) with galloyl chloride having the acetylated hydroxyl groups and the subsequent deprotection of the hydroxyl groups gave the desired hybrid compounds. Then, the antimicrobial activity of the compounds was evaluated using disc diffusion and minimum inhibitory concentration assays. Finally, the MTT assay was carried out to evaluate the cytotoxicity of the synthesized compounds on the mentioned cell lines. The structure of the synthesized compounds was elucidated by conventional spectroscopic methods such as NMR, FT-IR, and UV–Vis spectroscopy. All compounds prevented the growth of Staphylococcus coagulase more than the positive control of chloramphenicol, and one compound was more sensitive to the growth of Klebsiella pneumonia compared to the standard antibiotic. All compounds showed acceptable activity against cancer cells. The highest activity was observed against HeLa with an IC50 value of 3.2 μg/mL for compound 3d and against HCT116 with IC50 of 59.4 μg/mL for 3b. The high anticancer activity of compound 3d against HeLa allows us to consider it as a good lead compound for the development of new potent anticancer agents for the treatment of cervical cancer. Graphic abstract: [Figure not available: see fulltext.]

Novel tetrahydrobenzo[b]thiophen-2-yl)urea derivatives as novel α-glucosidase inhibitors: Synthesis, kinetics study, molecular docking, and in vivo anti-hyperglycemic evaluation

α-Glucosidase inhibitors, which can inhibit the digestion of carbohydrates into glucose, are one of important groups of anti-type 2 diabetic drugs. In the present study, we report our effort on the discovery and optimization of α-glucosidase inhibitors with tetrahydrobenzo[b]thiophen-2-yl)urea core. Screening of an in-house library revealed a moderated α-glucosidase inhibitors, 5a, and then the following structural optimization was performed to obtain more efficient derivatives. Most of these derivatives showed increased inhibitory activity against α-glucosidase than the parental compound 5a (IC50 of 26.71 ± 1.80 μM) and the positive control acarbose (IC50 of 258.53 ± 1.27 μM). Among them, compounds 8r (IC50 = 0.59 ± 0.02 μM) and 8s (IC50 = 0.65 ± 0.03 μM) were the most potent inhibitors, and showed selectivity over α-amylase. The direct binding of both compounds with α-glucosidase was confirmed by fluorescence quenching experiments. Kinetics study revealed that these compounds were non-competitive inhibitors, which was consistent with the molecular docking results that compounds 8r and 8s showed high preference to bind to the allosteric site instead of the active site of α-glucosidase. In addition, compounds 8r and 8s were not toxic (IC50 > 100 μM) towards LO2 and HepG2 cells. Finally, the in vivo anti-hyperglycaemic activity assay results indicated that compounds 8r could significantly decrease the level of plasma glucose and improve glucose tolerance in SD rats treated with sucrose. The present study provided the tetrahydrobenzo[b]thiophen-2-yl)urea chemotype for developing novel α-glucosidase inhibitors against type 2 diabetes.