67171-55-5

Basic information

• Product Name: METHYL 2-AMINO-4-PHENYLTHIOPHENE-3-CARBOXYLATE
• Synonyms: TIMTEC-BB SBB006989;2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER;AKOS 93440;AKOS B000760;AKOS BBS-00000797;3-THIOPHENECARBOXYLIC ACID, 2-AMINO-4-PHENYL-, METHYL ESTER;METHYL 2-AMINO-4-PHENYL-3-THIOPHENECARBOXYLATE;METHYL 2-AMINO-4-PHENYLTHIOPHENE-3-CARBOXYLATE
• CAS NO: 67171-55-5
• Molecular Formula: C₁₂H₁₁NO₂S
• Molecular Weight: 233.29
• Mol File: 67171-55-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 140-142°C
• Boiling Point: 379.5 °C at 760 mmHg
• Flash Point: 183.3 °C
• Appearance: /
• Density: 1.265 g/cm³
• CAS DataBase Reference: METHYL 2-AMINO-4-PHENYLTHIOPHENE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-AMINO-4-PHENYLTHIOPHENE-3-CARBOXYLATE(67171-55-5)
• EPA Substance Registry System: METHYL 2-AMINO-4-PHENYLTHIOPHENE-3-CARBOXYLATE(67171-55-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 67171-55-5(Hazardous Substances Data)

Usage

Uses

methyl 2-amino-4-phenylthiophene-3-carboxylate is a useful reactant for the synthesis thienopyrimidine-based FLT3 inhibitors.

Upstream product

• 98-86-2 acetophenone 
• 105-34-0 methyl 2-cyanoacetate 
• 14505-27-2 Methyl-α-cyano-β-methyl-β-phenylacrylat 

Downstream Products

• 126080-22-6 2-[3-(2-Chloro-ethyl)-ureido]-4-phenyl-thiophene-3-carboxylic acid methyl ester 
• 935759-47-0 4-oxo-5-phenyl-N-{3-[2-(1H-1,2,4-triazol-3-yloxy)ethoxy]-benzyl}-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide 
• 935760-34-2 ethyl 4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate 
• 76872-75-8 5-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione 
• 1622230-19-6 C₁₈H₁₃N₃OS 
• 1622230-18-5 C₂₀H₁₇N₃OS 
• 1622230-17-4 C₁₉H₁₄N₂O₂S 
• 1622230-24-3 C₁₈H₁₅N₅S 
• 1622230-23-2 C₂₀H₁₉N₅S 
• 1622230-22-1 C₁₉H₁₆N₄OS 

Relevant articles and documents

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.

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.

Synthesis and biological evaluation of novel thieno[2,3-d[pyrimidine-based FLT3 inhibitors as anti-leukemic agents

The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML. A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents.