162959-93-5

Basic information

• Product Name: 1-(thiophen-2-yl)cyclopropanecarbonitrile
• Synonyms: 1-(thiophen-2-yl)cyclopropanecarbonitrile;Cyclopropanecarbonitrile, 1-(2-thienyl)-;1-Thien-2-ylcyclopropanecarbonitrile;1-(thiophen-2-yl)cyclopropane-1-carbonitrile
• CAS NO: 162959-93-5
• Molecular Formula: C8H7NS
• Molecular Weight: 149.21288
• Mol File: 162959-93-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(thiophen-2-yl)cyclopropanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(thiophen-2-yl)cyclopropanecarbonitrile(162959-93-5)
• EPA Substance Registry System: 1-(thiophen-2-yl)cyclopropanecarbonitrile(162959-93-5)

Safety Data

• Hazardous Substances Data: 162959-93-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(thiophen-2-yl)cyclopropanecarbonitrile is used as a reactant for the synthesis of quinolines, which are a class of nitrogen-containing heterocyclic compounds with diverse biological activities. In particular, these quinolines serve as P-selectin inhibitors, playing a crucial role in the potential treatment of vascular diseases by modulating the inflammatory response and preventing the adhesion of leukocytes to the endothelium.

Upstream product

• 20893-30-5 2-cyanomethylthiophene 
• 5197-95-5 benzyltriethylammonium bromide 
• 106-93-4 ethylene dibromide 
• 107-04-0 1-Bromo-2-chloroethane 

Downstream Products

• 162959-94-6 1-(thien-2-yl)cyclopropanecarboxylic acid 
• 1429308-66-6 9a'-phenyl-7',8',9',9a'-tetrahydro-5'H-spiro[cyclopropane-1,4'-thieno[2,3-g]indolizin]-5'-one 

Relevant articles and documents

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

Efficient cyclopropanation of aryl/heteroaryl acetates and acetonitriles with vinyl diphenyl sulfonium triflate

A convenient method was developed for the cyclopropanation of aryl acetates and aryl acetonitrile using vinyl diphenyl sulfonium triflate salt. The newly developed conditions are simple, mild, and compatible with a wide range of functional groups, without the need to apply an inert atmosphere, or alkali bases.

GLP-1 RECEPTOR MODULATORS

Compounds are provided that modulate the glucagon-like peptide 1 (GLP-1) receptor, as well as methods of their synthesis, and methods of their therapeutic and/or prophylactic use. Such compounds can act as modulators or potentiators of GLP-1 receptor on their own, or with incretin peptides such as GLP-1(7-36) and GLP-1(9-36), or with peptide-based therapies, such as exenatide and liraglutide, and have the following general structure (where "^^^^" represents either or both the R and S form of the compound) (I) where A, B, C, Y1, Y2, Z, R1, R2, R3, R4, R5, W1, n, p and q are as defined herein.

A cascade approach to fused indolizinones through Lewis acid-copper(i) relay catalysis

A relay catalytic cascade process involving Lewis acid triggered ring-opening of cyclopropyl ketones with nitriles, the copper(i)-catalyzed Ritter process, and acid-promoted N-acyliminium ion cyclization is described, which efficiently provides thieno-, furano-, and benzo-indolizinones in moderate to good yields. The Royal Society of Chemistry 2013.

HETEROCYCLIC COMPOUND

Provided is a compound useful for the prophylaxis or treatment of cancer. The present invention relates to a compound represented by formula (I): wherein each symbol in the formula is as defined in the specification, or a salt thereof or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer.

Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8- (trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury

Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure-activity studies in this series by branching at the α position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.

Methods and Compositions for Selectin Inhibition

The present teachings relate to novel compounds of formula I: wherein the constituent variables are as defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selecting. Methods for treating or preventing selectin-mediated disorders are provided, which include administration of these compounds in a therapeutically effective amount.

TRIAZOLE DERIVATIVE OR SALT THEREOF

[Problem] There is provided a compound which can be used for therapy of diseases in which 11 β-hydroxysteroid dehydrogenase type 1(11β-HSD1) participates, in particular diabetes, insulin resistance. [Means for Solution] It has been found that a triazole derivative wherein the triazole ring is substituted with a trisubstituted methyl group in the 2-position or a pharmaceutically acceptable salt thereof has a strong 11β-HSD1 inhibitory activity. Moreover, the triazole derivative of the invention exhibits an excellent blood-glucose level-lowering action and hence can be used for therapy of diabetes, insulin resistance.

Antibacterial agents

The present invention provides compounds of formula (I): wherein R1-R6 and J and K have any of the values defined in the specification, and pharmaceutically acceptable salt thereof, that are useful as antibacterial agents. Also disclosed are pharmaceutical compositions comprising one or more compounds of formula I, processes for preparing compounds of formula I, and intermediates useful for preparing compounds of formula I.

Therapeutic agents

Tetrahydroisoquinoline compounds of formula I STR1 and pharmaceutically acceptable salts thereof, in which: R1 represents one or more substituents selected from H, halo, hydroxy, alkyl (optionally substituted by hydroxy), alkoxy, alkylthio, alk