85716-87-6

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE is used as an active pharmaceutical ingredient for its potential biological activities, such as its antimicrobial, antifungal, and anticancer properties. Its unique chemical structure allows it to target specific biological pathways, making it a valuable compound in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE is used as a reagent in chemical reactions. Its isothiocyanate functional group enables it to react with various organic compounds, facilitating the synthesis of complex molecules and contributing to the advancement of organic chemistry.
Used in Chemical Research:
ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE is also used in chemical research as a model compound to study the properties and reactivity of isothiocyanates. Its unique structure and biological activities make it an interesting subject for researchers to explore and understand the underlying mechanisms of its actions.
Safety Precautions:
Due to its strong odor and potential reactivity, ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE should be handled with care. It should be stored in a cool, dry place away from direct sunlight and sources of ignition to prevent any hazardous incidents. Proper safety measures, such as wearing protective clothing and using appropriate containment, should be followed during its use in laboratories or industrial settings.

InChI:InChI=1/C12H13NO2S2/c1-2-15-12(14)10-8-5-3-4-6-9(8)17-11(10)13-7-16/h2-6H2,1H3

Upstream product

• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 463-71-8 thiophosgene 
• 75-15-0 carbon disulfide 
• 90543-03-6 4,5,6,7-Tetrahydro-2-(triphenylphosphoranylidenamino)benzothiophen-3-carbonsaeure-ethylester 
• 105-56-6 ethyl 2-cyanoacetate 
• 108-94-1 cyclohexanone 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 

Downstream Products

• 105544-70-5 ethyl 2-(4-methylpiperazine-1-carbothioamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 109315-56-2 2-[3-(3-Ethoxycarbonyl-4-phenyl-thiophen-2-yl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 105544-62-5 N-(3-carboethoxy-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-N-thiourea 
• 151094-90-5 2,3,5,6,7,8-hexahydro-3-amino-2-thioxo<1>benzothieno<2,3-d>pyrimidin-4(1H)-one 
• 105544-64-7 2-(3-Cyclohexyl-thioureido)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 105544-65-8 2-[3-(4-Carboxy-phenyl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 105544-68-1 2-(3,3-Diethyl-thioureido)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 109315-49-3 2-[3-(4-Ethoxycarbonyl-phenyl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 175599-96-9 2-[3-(2-Chloro-phenyl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 207743-82-6 2-(3-Cyclohexyl-3-methyl-thioureido)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 380342-95-0 2-[3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 380343-29-3 2-[3-(4-difluoromethoxy-phenyl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 746653-39-4 2-[3-(2-methoxy-phenyl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 398996-92-4 2-[3-(2,4-dichloro-phenyl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of urea analogues bearing N-alkyl-N’-(thiophen-2-yl) scaffold and evaluation of their innate immune response to toll-like receptors

Previous high throughput virtual screening of 10 million-compound and following cell based validation led to the discovery of a novel, nonlipopeptide-like chemotype ZINC 6662436, as toll-like receptor 2 (TLR2) agonists. In this report, compounds belonging

Enterovirus inhibitory activity of C-8-tert-butyl substituted 4-aryl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-ones

Members of a series of 4-aryl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-ones (1, Fig. 2) were prepared and tested against representative enteroviruses including Human Coxsackievirus B1 (Cox B1), Human Coxsackievirus B3 (Cox B3), human Poliovirus 3 (PV3), human Rhinovirus 14 (HRV14), human Rhinovirus 21 (HRV 21) and human Rhinovirus 71 (HRV 71). The C-8-tert-butyl group on the tetrahydrobenzene ring in these substances was found to be crucial for their enterovirus activity. One member of this group, 1e, showed single digit micromolar activities (1.6–8.85?μM) against a spectrum of viruses screened, and the highest selectivity index (SI) values for Cox B1 (>11.2), for Cox B3 (>11.5), and for PV3 (>51.2), respectively. In contrast, 1p, was the most active analog against the selected HRVs (1.8–2.6?μM), and showed the highest selectivity indices among the group of compounds tested. The SI values for 1p were 11.5 for HRV14, 8.4 for HRV21, and 12.1 for HRV71, respectively.

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).

Facile and versatile synthesis of alkyl and aryl isothiocyanates by using triphosgene and cosolvent

A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH 3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Discovery of a novel 5-HT3 antagonist/5-HT1A agonist 3-amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl} quinazolin-4(3 H)-one (TZB-30878) as an orally bioavailable agent for irritable bowel syndrome

We have prepared a series of quinazolinone derivatives linked with piperazinylquinoline for the treatment of irritable bowel syndrome (IBS). Using pharmacophore analysis, we designed and synthesized compounds which bind to both serotonin receptor subtype 1A (5-HT1A) and subtype 3 (5-HT 3). Quinazolinone derivatives with a sulfur atom in the linker showed high affinity in in vitro assays, but low in vivo activity. Focusing on the linker to improve the pharmacokinetic profile, the sulfur atom in the linker was replaced with a methylene group. Further optimization led to the discovery of compound 17m (TZB-30878) (J. Pharmacol. Exp. Ther. 2007, 322, 1315 -1323, Patent WO2005082887 (A1), 2005), a novel 5-HT1A agonist/5-HT3 antagonist in the 3-aminoquinazolinone series. In in vivo functional assays, 17m dose dependently inhibited the Bezold-Jarisch reflex and induced 5-HT 1A-mediated behaviors, and in an IBS animal model, 17m significantly inhibited stress-induced defecation. Pretreatment by WAY-100635 (5-HT 1A antagonist) significantly attenuated but did not abolish the inhibitory effects of 17m. These results suggested that 17m exerted inhibitory effects via both 5-HT1A agonistic and 5-HT3 antagonistic activities and that 17m would be useful as a therapeutic agent for IBS.

Facile synthesis of 2-alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]- Pyrimidin-4(3H)-ones

Isothiocyanate 2, obtained from aza-Wittig reaction of iminophosphorane 1 with CS2, reacted with amine to give 2-thioxo-2,3,5,6,7,8- hexahydrobenzothieno[2,3-d]pyrimidin-4(1H)-ones 4 in the presence of sodium ethoxide. S-Alkylation of 4 produced 2-alkylth

Pyrimido-Benzimidazole Derivatives and the Use Thereof in the Form of Agonists and Antagonists of Melanocortin Receptors

The invention relates to novel pyrimido-benzimidazole derivatives. Said products exhibit a good affinity for certain melanocortin receptor sub-types, in particular MC4 receptors. Said products represent a particular interest for treating pathological disorders and diseases associated with one or several melanocortin receptors. Pharmaceutical compositions containing said products and the use thereof for a drug preparation are also disclosed.

Synthetic approaches to bridgehead nitrogen methanesulfonamide derivatives of 3-amino-2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones, potential COX-2 selective inhibitors

Methane sulfonamide derivatives of 3-amino-2-thioxo-2,3-dihydrothieno[2,3- d]pyimidin-4(1H)-one, potential selective COX-2 inhibitors, were synthesized and their structural elucidation is here reported. Some derivatives, at 10 μM concentration, showed a s

Synthesis of certain new thieno[2,3-d] pyrimidines as potential antitumor and radioprotective agents

During research on anticancer and radioprotective heterocyclic compounds containing thiophene ring 5-10, 15, 19, thieno[2,3-d]pyrimidines 11-14 and bis-compound having thieno[2,3-d]pyrimidine 18 were synthesized. The synthesized compounds were characteriz