166591-62-4

Basic information

• Product Name: 5-(3-METHYLPHENYL)-2-THIOPHENECARBOXYLIC ACID
• Synonyms: AKOS BAR-1231;5-(3-METHYLPHENYL)-2-THIOPHENECARBOXYLIC ACID
• CAS NO: 166591-62-4
• Molecular Formula: C₁₂H₁₀O₂S
• Molecular Weight: 218.27
• Mol File: 166591-62-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 393.4±30.0 °C(Predicted)
• Appearance: /
• Density: 1.261±0.06 g/cm3(Predicted)
• PKA: 3.50±0.10(Predicted)
• CAS DataBase Reference: 5-(3-METHYLPHENYL)-2-THIOPHENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-METHYLPHENYL)-2-THIOPHENECARBOXYLIC ACID(166591-62-4)
• EPA Substance Registry System: 5-(3-METHYLPHENYL)-2-THIOPHENECARBOXYLIC ACID(166591-62-4)

Safety Data

• Hazardous Substances Data: 166591-62-4(Hazardous Substances Data)

Upstream product

• 38401-69-3 5-(3-methylphenyl)-2-thiophenecarboxaldehyde 
• 7311-63-9 5-bromothiophene-2-carboxylic acid 
• 17933-03-8 m-tolylboronic acid 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 

Downstream Products

• 1027426-80-7 5-m-Tolyl-thiophene-2-carbonyl chloride 
• 1025871-45-7 5-(3-methylphenyl)-2-thiophenecarboxylic acid, N-tert-butylamide 

Relevant articles and documents

Broadening antifungal spectrum and improving metabolic stablity based on a scaffold strategy: Design, synthesis, and evaluation of novel 4-phenyl-4,5-dihydrooxazole derivatives as potent fungistatic and fungicidal reagents

5-phenylthiophene derivatives exhibited excellent antifungal activity against Candida albicans, Candida tropicalis and Cryptococcus neoformans. However, optimal compound 7 was inactive against Aspergillus fumigatus and unstable in human liver microsomes in vitro with a half-life of 18.6 min. To discover antifungal agents with a broad spectrum and improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of 4-phenyl-4,5-dihydrooxazole derivatives were designed and synthesized. It was especially encouraging that compound 22a displayed significant antifungal activities against eight susceptible strains and seven FLC-resistant strains. Furthermore, the potent compound 22a could prevent the formation of fungalbiofilms and displayed satisfactory fungicidal activity. In addition, the metabolic stability of compound 22a was improved significantly, with the half-life of 70.5 min. Compound 22a was almost nontoxic to mammalian A549, MCF-7, HepG2, and 293T cells. Moreover, pharmacokinetic studies in SD rats showed that compound 22a exhibited pharmacokinetic properties with a bioavailability of 15.22% and a half-life of 4.44 h, indicating that compound 22a is worthy of further study.

Substituted hexahydrobenzo[f]thieno[c]quinolines as dopamine D1- selective agonists: Synthesis and biological evaluation in vitro and in vivo

A series of substituted 9,10- dihydroxyhexahydrobenzo[f]thieno[c]quinolines (TB[f]Q), varying with respect to the position of the thiophene relative to the benzo[f]quinoline core and the nature and position of the substituent on the thiophene, were prepared and evaluated for their affinity and selectivity for the dopamine D1-like receptor. The thieno[3,2-c]B[f]Q regioisomers bearing a small alkyl (C1-C3) substituent at the 2 position were potent (K(i) 50) D1 agonists with close to full agonist activity (IA > 85%). The compounds were resolved and found to exhibit a high level of enantiospecificity in their interaction with the D1 receptor. Selected compounds were tested in vivo in the 6-OHDA rodent model of Parkinson's disease and for their liability to produce seizure-like activities in mice. (5aR)-trans-2-Propyl-4,5,5a,6,7,11b-hexahydro-3-thia-5-azacyclopent-1- ena[c]phenanthrene-9,10-diol (5) emerged as the compound with the best overall in vivo profile in terms of potency (ED50 = 0.04 μmol/kg) and safety.