61325-02-8

Usage

Uses

Used in Organic Synthesis:
Methyl 2-amino-5-phenylthiophene-3-carboxylate is used as a synthetic intermediate for the preparation of a variety of organic compounds. Its unique structure allows for further chemical reactions and modifications, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2-amino-5-phenylthiophene-3-carboxylate is used as a key intermediate in the synthesis of certain drugs. Its presence in the molecular structure can contribute to the development of new therapeutic agents with potential applications in various medical fields.
Used in Chemical Research:
Methyl 2-amino-5-phenylthiophene-3-carboxylate is also used in chemical research as a model compound to study the reactivity and properties of thiophenes and their derivatives. This can lead to a better understanding of the underlying chemical mechanisms and the development of new synthetic strategies.

InChI:InChI=1/C12H11NO2S/c1-15-12(14)9-7-10(16-11(9)13)8-5-3-2-4-6-8/h2-7H,13H2,1H3

Upstream product

• 122-78-1 phenylacetaldehyde 
• 105-34-0 methyl 2-cyanoacetate 
• 570419-61-3 C₁₂H₁₁NO₂ 
• 1262235-61-9 methyl 2-amino-5-phenyl-4,5-dihydrothiophene-3-carboxylate 
• 479617-68-0 methyl 1-cyano-2-phenylcyclopropanecarboxylate 
• 3709-20-4 dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate 

Downstream Products

• 126080-23-7 2-[3-(2-Chloro-ethyl)-ureido]-5-phenyl-thiophene-3-carboxylic acid methyl ester 
• 76575-34-3 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid 
• 76575-56-9 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide 
• 126080-20-4 3-(2-Hydroxy-ethyl)-6-phenyl-1H-thieno[2,3-d]pyrimidine-2,4-dione 
• 859204-50-5 5-phenyl-2-(tetrahydro-2H-thiopyran-4-ylamino)thiophen-3-carboxylic acid methyl ester 
• 86126-60-5 6-phenylthieno<2,3-d>pyrimidine-2,4-dione 
• 923010-20-2 methyl 2-[(tert-butoxycarbonyl)amino]-5-phenylthiophene-3-carboxylate 
• 1219458-48-6 C₂₄H₂₃N₃O₂S 
• 886522-22-1 C₁₆H₁₃NO₅S 
• 38695-72-6 methyl 5-phenylthiophene-3-carboxylate 
• 1187467-82-8 2-bromo-5-phenyl-thiophene-3-carboxylic acid 
• 1402143-79-6 methyl 2-(2-bromo-5-phenylthiophen-3-yl)-2-(tert-butoxy)acetate 
• 1402143-80-9 methyl 2-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-5-phenylthiophen-3-yl]acetate 
• 1402143-74-1 2-(tert-butoxy)-2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-5-phenylthiophen-3-yl]acetic acid 

Relevant academic research and scientific papers

Microwave-assisted synthesis of 2-aminothiophene derivatives via improved gewald reactions

In this paper, a new and efficient method was developed to prepare 2-aminothiophene derivatives through improved Gewald reaction. Thirty-one final products were synthesized under microwave radiation for 30 min with 57%-95% isolated yields. All the product

Synthesis of novel 2-(1-adamantanylcarboxamido)thiophene derivatives. Selective cannabinoid type 2 (CB2) receptor agonists as potential agents for the treatment of skin inflammatory disease

A set of CB2R ligands, based on the thiophene scaffold, was synthesized and evaluated in in vitro assays. Compounds 8c-i, k, l, bearing the 3-carboxylate and 2-(adamantan-1-yl)carboxamido groups together with apolar alkyl/aryl substituents at 5-position or at 4- and 5-positions of the thiophene ring possess high CB2R affinity at low nanomolar concentration, good receptor selectivity, and agonistic functional activity. The full agonist 8g, showing the best balance between receptor affinity and selectivity, was tested in vitro in an experimental model of allergic contact dermatitis and proved to be able to block the release of MCP-2 in HaCaT cells at 10 μM concentration.

Thiourea participation in [3+2] cycloaddition with donor-acceptor cyclopropanes: A domino process to 2-amino-dihydrothiophenes

The Yb(OTf)3-catalyzed [3+2] cycloaddition of donor-acceptor cyclopropanes with thiourea offers an efficient route to diverse 2-amino-4,5-dihydrothiophenes (up to 92% yield), in which optically active 2-amino-dihydrothiophenes can be produced f

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands

Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.

Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor

The phosphatase PTP4A3 is an attractive anticancer target, but knowledge of its exact role in cells remains incomplete. A potent, structurally novel inhibitor of the PTP4A family was obtained by photooxygenation of a less active, electron-rich thienopyrid

Heteroarylpyrimindinedione derivative and use thereof

The invention provides a heteroarylpyrimindinedione derivative and use thereof. The heteroarylpyrimindinedione derivative comprises a compound with a structure shown as general formula I, and a pharmaceutically acceptable salt or hydrate thereof. The derivative is obtained by chemical synthesis, and pharmacological experiments prove that the active ligand with cannabinoid type II receptor CB2 can be used for preparation of drugs for prevention and mitigation of CB2 receptor-mediated diseases, and the drug is cannabinoid CB2 receptor agonist's agonist, partial agonist, inverse agonist or antagonist. And the general structural formula I is shown as the specification.

INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES

The present invention relates to compounds of formula (1) as claimed in claim 1, their use in the treatment or the prevention of viral disorders, including HIV. (Formula I)

Synthesis of functionalized dihydrothiophenes from doubly activated cyclopropanes using tetrathiomolybdate as the sulfur transfer reagent

A number of doubly activated cyclopropanes were synthesized starting from various substituted bromosulfonium bromides in good yield. Regioselective ring-opening of cyclopropanes with tetrathiomolybdate as the sulfur transfer reagent gave dihydrothiophenes

1,4-Thienodiazepine-2,5-diones via MCR (I): Synthesis, Virtual Space and p53-Mdm2 Activity

1,4-Thienodiazepine-2,5-diones have been synthesized via the Ugi-Deprotection-Cyclization (UDC) approach starting from Gewald 2-aminothiophenes in a convergent and versatile manner. The resulting scaffold is unprecedented, cyclic, and peptidomimetic with four points of diversity introduced from readily available starting materials. In addition to eighteen synthesized and characterized compounds, a virtual compound library was generated and evaluated for chemical space distribution and drug-like properties. A small focused compound library of 1,4-thienodiazepine-2,5-diones has been screened for the activity against p53-Mdm2 interaction. Biological evaluations demonstrated that some compounds exhibited promising antagonistic activity.