60442-41-3

Usage

Uses

Used in Pharmaceutical Synthesis:
ETHYL 2-[(2-CHLOROACETYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE is used as an intermediate in the synthesis of various pharmaceuticals for its potential biological activity, contributing to the development of new drugs with therapeutic benefits.
Used in Agrochemical Production:
In the agrochemical industry, ETHYL 2-[(2-CHLOROACETYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE serves as an intermediate in the production of various agrochemicals, potentially enhancing crop protection and management strategies.
Used in Medicinal Chemistry Research:
ETHYL 2-[(2-CHLOROACETYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE is utilized in medicinal chemistry research to explore its properties and potential applications in drug development, including the creation of novel therapeutic agents.
It is crucial to handle ETHYL 2-[(2-CHLOROACETYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE with appropriate safety measures and to follow established protocols during its use in any application to ensure the safety of both individuals and the environment.

InChI:InChI=1/C13H16ClNO3S/c1-2-18-13(17)11-8-5-3-4-6-9(8)19-12(11)15-10(16)7-14/h2-7H2,1H3,(H,15,16)

Upstream product

• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 79-04-9 chloroacetyl chloride 
• 6802-76-2 ethyl 2-cyano-2-cyclohexylideneacetate 
• 108-94-1 cyclohexanone 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 62349-05-7 ethyl 2-[(2-morpholinoacetyl)amino]-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate 
• 62349-04-6 2-(2-piperidin-1-yl-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 54968-59-1 (6,7-tetramethylene-1-oxo-1,2-dihydrothieno[2,3-d]pyrimidin-3-ylsulfanyl)acetic acid ethyl ester 
• 1415716-72-1 C₁₄H₁₉N₃O₃S₂*ClH 
• 1447585-64-9 ethyl 2-({[(5-{[(4-methylphenyl)amino]carbonyl}-2-{2-[(4-methylphenyl)amino]-2-oxoethyl}pyrimidin-4-yl)thio]acetyl}amino)-4,5,6,7-tetrahydro-1-benzo[b]thiophene-3-carboxylate 
• 1420294-22-9 ethyl 2-(2-(4-(2-fluorobenzyl)piperazin-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 496777-64-1 ethyl 2-(2-(4-(4-methoxyphenyl)piperazin-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 309945-60-6 ethyl 2-(2-(4-benzylpiperazin-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 698980-13-1 ethyl 2-(2-(4-benzylpiperidin-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 96334-44-0 2-amino-3-ethoxycarbonyl-7-oxo-4,5,6,7-tetrahydrobenzothiophene 
• 96334-46-2 7-oxo-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid 

Relevant academic research and scientific papers

Discovery of new apoptosis-inducing agents for breast cancer based on ethyl 2-amino-4,5,6,7-tetra hydrobenzo[b]thiophene-3-carboxylate: Synthesis, in vitro, and in vivo activity evaluation

A multicomponent synthesis was empolyed for the synthesis of ethyl 2-amino-4,5,6,7- tetrahydrobenzo[b]thiophene-3-carboxylate 1. An interesting cyclization was obtained when the amino-ester 1 reacted with ethyl isothiocyanate to give the benzo[4,5]thieno[

Substituted chloroacetamides as potential cancer stem cell inhibitors: Synthesis and biological evaluation

Cancer kills, irrespective of geographical and cultural origin. Novel modalities for treating cancer are desperately needed. Cancer stem cells (CSCs), main culprits behind chemoresistance and tumor relapse, are one of the few logical choices. Herein, we r

Novel thiazole-thiophene conjugates as adenosine receptor antagonists: Synthesis, biological evaluation and docking studies

Here we report novel thiazole-thiophene conjugates as adenosine receptor antagonists. All the molecules were evaluated for their binding affinity for adenosine receptors. Most of the molecules were found to interact with the A1, A2A and A3 adenosine receptor subtypes with good affinity values. The most potent and selective compound 8n showed an A3 Ki value of 0.33 μM with selectivity ratios of >90 versus the A1 and >30 versus the A2 subtypes. For compound 8n docking studies into the binding site of the A3 adenosine receptor are provided to visualize its binding mode.

Tracing binding modes in hit-to-lead optimization: Chameleon-like poses of aspartic protease inhibitors

Successful lead optimization in structure-based drug discovery depends on the correct deduction and interpretation of the underlying structure-activity relationships (SAR) to facilitate efficient decision-making on the next candidates to be synthesized. Consequently, the question arises, how frequently a binding mode (re)-validation is required, to ensure not to be misled by invalid assumptions on the binding geometry. We present an example in which minor chemical modifications within one inhibitor series lead to surprisingly different binding modes. X-ray structure determination of eight inhibitors derived from one core scaffold resulted in four different binding modes in the aspartic protease endothiapepsin, a well-established surrogate for e.g. renin and β-secretase. In addition, we suggest an empirical metrics that might serve as an indicator during lead optimization to qualify compounds as candidates for structural revalidation.

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).

Synthesis and reactions of some heterocyclic candidates based on 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene moiety as anti-arrhythmic agents

In continuation of our previous work, a series of novel thiophene derivatives 4-16 were synthesized by the reaction of ethyl 2-amino-4,5,6,7- tetrahydrobenzo[b]thiophene-3-carboxylate (1) or 2-amino-4,5,6,7- tetrahydrobenzo[b]thiophene-3-carbonitrile (2)

Design, synthesis, and x-ray analysis of a glycoconjugate bound to mycobacterium tuberculosis antigen 85C

Tuberculosis (TB) is a global health threat with nearly 500 000 new cases of multidrug-resistant TB estimated to occur every year, so new drugs are desperately needed. A number of current antimycobacterial drugs work by interfering with the biosynthesis of key components of the mycolylarabinogalactan (mAG). In light of this observation, other enzymes involved in the synthesis of the mAG should also serve as targets for antimycobacterial drug development. One potential target is the Antigen 85 (Ag85) complex, a family of mycolyltransferases that are responsible for the transfer of mycolic acids from trehalose monomycolate (TMM) to the arabinogalactan. Virtual thiophenyl-arabinoside conjugates were docked to antigen Ag85C (PDB code: 1va5) using Glide. Compounds with good docking scores were synthesized by a Gewald synthesis followed by linking to 5-thioarabinofuranosides. The resulting thiophenyl-thioarabinofuranosides were assayed for inhibition of mycoyltransferase activity using a 4-methylumbelliferyl butyrate fluorescence assay. The conjugates showed K i values ranging from 18.2 to 71.0 μM. The most potent inhibitor was soaked into crystals of Mycobacterium tuberculosis antigen 85C and the structure of the complex determined. The X-ray structure shows the compound bound within the active site of the enzyme with the thiophene moiety positioned in the putative α-chain binding site of TMM and the arabinofuranoside moiety within the known carbohydrate-binding site as exhibited for the Ag85B-trehalose crystal structure. Unexpectedly, no specific hydrogen bonding interactions are being formed between the arabinofuranoside and the carbohydrate-binding site of the active site suggesting that the binding of the arabinoside within this structure is driven by shape complementarily between the arabinosyl moiety and the carbohydrate binding site.

Synthesis and analgesic activities of some 2-(benzazolylacetyl)amino-3- ethoxycarbonylthiophene derivatives

In this study, some 2-[2-(benzazole-2-thioxy)acetylamino]-3- ethoxycarbonylthiophene and 2-[2-(benzazole-1-yl)acetylamino]-3- ethoxycarbonylthiophene compounds were obtained by the reaction of 2-chloroacetylamino-3-ethoxycarbonylthiophene derivatives and a suitable benzazole-2-thione or benzimidazole derivatives. Analgesic activities of the compounds were tested by using tail-flick and tail-immersion methods. It is reported that some of the compounds showed remarkable analgesic activities. Copyright Taylor & Francis Inc.

ANTHELMINTIC AND INSECTICIDAL THIOPHENE DERIVATIVES

Novel anthelmintic compositions containing thiophene derivatives as active ingredients are disclosed.

New syntheses of 2-alkylthio-4-oxo-3,4-dihydroquinazolines, 2-alkylthioquinazolines, as well as their hetero analogues

N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-4-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with amines.