2048-57-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Thienyl isocyanate is used as a key intermediate in the synthesis of pharmaceuticals for its ability to react with various functional groups, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Thienyl isocyanate is utilized as a precursor in the production of pesticides and other crop protection agents, enhancing agricultural productivity and crop protection.
Used in Dye Industry:
2-Thienyl isocyanate is also employed in the dye industry, where it serves as a building block for the creation of novel dyes with specific color properties and applications in various industries, such as textiles and printing.
Used in Organic Synthesis:
2-Thienyl isocyanate is used as a versatile intermediate in organic synthesis, enabling the formation of a wide range of organic compounds with diverse applications across different industries.
Precaution:
Given its hazardous nature, 2-Thienyl isocyanate can cause irritation to the skin, eyes, and respiratory system. Therefore, it is imperative to exercise caution and use appropriate protective equipment and handling procedures when working with this chemical to ensure safety.

InChI:InChI=1/C5H3NOS/c7-4-6-5-2-1-3-8-5/h1-3H

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 4648-54-8 trimethylsilylazide 
• 2046-39-1 2-thiophenecarbonyl azide 
• 527-72-0 2-thiophenylcarboxylic acid 
• 17698-15-6 N-hydroxythiophene-2-carboxamide 

Downstream Products

• 1173204-76-6 1-[4-(3-ethyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)phenyl]-3-(2-thienyl)urea 
• 1173205-27-0 1-(4-(3-cyclopropyl-7-morpholino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)phenyl)-3-(thiophen-2-yl)urea 
• 1173206-07-9 1-{4-[7-morpholin-4-yl-3-(2,2,2-trifluoroethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]phenyl}-3-(2-thienyl)urea 
• 1173205-95-2 tert-butyl 3-(7-morpholin-4-yl-5-{4-[(2-thienylcarbamoyl)amino]phenyl}-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)azetidine-1-carboxylate 
• 903150-00-5 C₁₁H₉BrN₂OS 
• 1173206-95-5 1-[4-(3-methyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)phenyl]-3-(2-thienyl)urea 
• 791717-59-4 5-benzyl-4-(2-thienyl)-2,4-dihydro-[1,2,4]triazole-3-one 
• 139210-20-1 (E)-3-[2-(Thiophen-2-yliminomethyleneamino)-phenyl]-acrylic acid ethyl ester 
• 139210-19-8 (E)-3-[2-(Thiophen-2-yliminomethyleneamino)-phenyl]-acrylic acid methyl ester 

Relevant academic research and scientific papers

ISOINDOLINONE COMPOUNDS

Disclosed herein is a compound or pharmaceutically acceptable salts or stereoisomers thereof of of formula I wherein X1 is linear or branched C1-6 alkyl, C3-6 cycloalkyl, -C1-6 alkyl C3-6 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, C1-6 alkyl C6-10 aryl, C1-6 alkyl 5-10 membered heteroaryl, wherein X1 is unsubstituted or substituted with one or more of halogen, linear or branched C1-6 alkyl, linear or branched C1-6 heteroalkyl, CF3, CHF2, -O-CHF2, -O-(CH2)2-OMe, OCF3, C1-6 alkylamino, -CN, -N(H)C(O)-C1- 6alkyl, -OC(O)-C1-6alkyl, -OC(O)-C1-4alkylamino, -C(O)O-C1-6alkyl, -COOH, - CHO, -C1-6alkylC(O)OH, -C1-6alkylC(O)O-C1-6alkyl, NH2, C1-6 alkoxy or C1-6 alkylhydroxy; X2 is hydrogen, C6-10 aryl, 5-10 membered heteroaryl, -O-(5-10 membered heteroaryl), 4-8 membered heterocycloalkyl, C1-4 alkyl 4-8 membered heterocycloalkyl, -O-(4-8 membered heterocycloalkyl), -O-C1-4 alkyl-(4-8 membered heterocycloalkyl), -OC(O)-C1-4alkyl-4-8 membered heterocycloalkyl or C6 aryloxy, wherein X2 is unsubstituted or substituted with one or more of linear or branched C1-6 alkyl, NH2, NMe2 or 5-6 membered heterocycloalkyl; n is 0, 1 or 2.

COMPOUNDS FOR TREATING VIRAL INFECTIONS

The present invention relates to small molecule compounds and their use in the treatment of diseases, in particular viral diseases, in particular hepatitis C virus (HCV).

A simple, one-pot synthesis of N-Alkyl and N-aryl thieno[2,3-d] pyrimidinones from thiophene-and benzothiophene-2-yl-ureas

We herein describe a convenient, one-pot synthesis of N-substituted thieno and benzothieno[2,3-d]pyrimidinones from the respective thiophene-2-yl ureas. This intramolecular cyclization, which presumably proceeds via a Vilsmeier-Haack dimethyliminium inter

1-propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the Lossen rearrangement: Application to the synthesis of urea and carbamate derivatives

The synthesis of hydroxamic acids starting from carboxylic acids employing 1-propanephosphonic acid cyclic anhydride (T3P) activation is described. Application of ultrasonication accelerates this conversion. Further, the T3P has also been employed to activate the hydroxamates, leading to isocyanates via the Lossen rearrangement. The isocyanates were trapped with suitable nucleophiles to afford the corresponding ureas and carbamates. Georg Thieme Verlag Stuttgart New York.

New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: Application of peptide coupling agents EDC and HBTU

Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved. The Royal Society of Chemistry 2010.

2-Arylureidobenzoic Acids: Selective Noncompetitive Antagonists for the Homomeric Kainate Receptor Subtype GluR5

A series of 2-arylureidobenzoic acids (AUBAs) was prepared by a short and effective synthesis, and the pharmacological activity at glutamate receptors was evaluated in vitro and in vivo. The compounds showed noncompetitive antagonistic activity at the kainate receptor subtype GluR5. The most potent compounds showed more than 50-fold selectivity for GluR5 compared to GluR6 and the AMPA receptor subtypes GluR1-4. The structure-activity relationships for the AUBAs showed distinct structural requirements for the substituents on the two aromatic ring systems. Only para-substituents were tolerated on the benzoic acid moiety (ring A), whereas ring B tolerated a variety of substituents, but with a preference for lipophilic substituents. The most potent compounds had a 4-chloro substituent on ring A and 3-chlorobenzene (6b), 2-naphthalene (8h), or 2-indole (8k) as ring B and had IC50 values of 1.3, 1.2, and 1.2 μM, respectively, in a functional GluR5 assay. Compound 6c (IC50 = 4.8 μM at GluR5) showed activity in the in vivo ATPA rigidity test, indicating that 6c has better pharmacokinetic properties than 8h, which was inactive in this test. The AUBAs are the first example of a series of noncompetitive GluR5-selective antagonists and may prove to be important pharmacological tools and leads in the search for therapeutic glutamatergic agents.

Hypocholesterolemic agents

This invention relates to certain steroidal glycosides useful as hypocholesterolemic agents and antiatherosclerosis agents and certain protected intermediates useful in the preparation of said steroidal glycosides.

Boron-Containing Nucleosides. 1. Synthesis of the Novel Heterocycle 2-Benzyl-1,4-dihydro-1-hydroxythieno[3,2-c7] [1,5,2]diazaborin-3(2H)-one: A Thieno-fused 4-Borauracil

The synthesis of the novel boron-containing nucleobase 2-benzy]-1,4-dihydro-l-hydroxythieno[3,2-c]-[1,5,2]diazaborin-3(2H)-one (8), a thieno-fused 4-borauracil, is described. Compound 8 was prepared in three steps starting from 2-thiophenecarbonyl chlorid

Tyrosine kinase inhibitors. 4. Structure-activity relationships among N- and 3-substituted 2,2'-dithiobis(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases

A series of 3-substituted 2,2'-dithiobis(1H-indoles) were synthesized and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase, to extend the available structure-activity relationships for this series. The majority of the compounds were prepared either by reaction of 2-chloro-1-methylindole-3-carbonyl chloride with amines, followed by thiomethylation, demethylation, and oxidative dimerization, or by reaction of isocyanates with the anion of 1-methyl-2-indolinethione followed by dimerization. Overall, inhibitory activity is retained by analogues having a wide variety of side chains. A series of 3-carboxamide analogues had moderate to good activity against isolated EGFR (IC50s 1-20 μM), with monoalkyl substitution of the carboxamide being optimal. Polar side chains were generally less effective than lipophilic ones, with benzyl being particularly effective. However, N,N-disubstitution was the most effective pattern for inhibition of pp60(v-src). A variety of substituted N-phenylcarboxamides had lower activity against EGFR than the parent derivative, and a N- thienylcarboxamide also had low activity. A series of 3-ketones, including methyl, phenyl, and furyl derivatives, showed moderate activity against the pp60(v-src) kinase, but were less effective against EGFR. The mechanism of inhibition of both kinases by these drugs was shown to be noncompetitive with respect to both ATP and peptide substrate. Selected compounds inhibited the growth of Swiss 3T3 cells with IC50s in the low micromolar range and inhibited bFGF-mediated intracellular tyrosine phosphorylation in the same cell line. Thiol inhibits the effects of the compounds, suggesting that one possible mechanism of inhibition is thiol-disulfide exchange with thiol- containing residues in the catalytic sites. Crystal structures of two representative compounds show a folded, V-shaped structure, with the disulfide bridge exposed, consistent with this hypothesis.

Preparation and Cycloaddition of Thienyl Isocyanates with Trimethylsilyl Azide: One-pot Synthesis of Thienyltetrazolin-5-ones

Efforts to prepare thienyl isocyanates by thermal reactions of thenoyl chlorides with trimethylsilyl azide (TMSA) led preferentially to the formation of 1,4-disubstituted tetrazolin-5-ones, arising by interaction of the initially formed thienyl isocyanate with TMSA.In fact, 2-thenoyl chloride and benzothiophene-2-carbonyl chloride reacted with 1 equiv.TMSA in refluxing carbon tetrachloride to give 1-(2-thienyl or benzothienyl)-4-(2-thenoyl or benzothiophenecarbonyl)tetrazolin-5-one 4d, e, whereas 3-thenoyl chloride led to 1-(3-thienyl)-4-trimethylsilyltetrazolin-5-one adduct II which was converted, after hydrolytic desilylation, to 1-(3-thienyl)tetrazolin-5(4H)-one 4c.Similar reactions, carried out with more than two equiv. of TMSA, led in all cases to the formation of the corresponding 1-heteroaryltetrazolin-5-one 4a-c via the corresponding silylated tetrazolin-5-ones II, whereas at room temp. such reactions gave essentially thenoyl azides which, after elimination of the excess TMSA, were thermally converted to the corresponding thienyl isocyanates 3 in fairly good yields.