Production Method 1

14282-78-1

23806-24-8

28686-90-0

81452-54-2

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol

Reference

Synthesis of N-(methoxycarbonylthienylmethyl)thioureas and evaluation of their interaction with inducible and neuronal nitric oxide synthase

Suaifan, Ghadeer A. R. Y.; et al, Molecules, 2010, 15, 3121-3134

Production Method 2

28686-90-0

81452-54-2

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Hexane ;  0 °C; 3 h, 0 °C
1.2 Solvents: Diethyl ether ;  0 °C; 16 h, 0 °C
1.3 Reagents: Water ;  cooled

Reference

Synthesis of N-(methoxycarbonylthienylmethyl)thioureas and evaluation of their interaction with inducible and neuronal nitric oxide synthase

Suaifan, Ghadeer A. R. Y.; et al, Molecules, 2010, 15, 3121-3134

Methyl 4-methylthiophene-2-carboxylate Raw materials

• 4-Methylthiophene-2-carboxylic acid
• 3-Methylthiophene-2-carboxylic acid

Methyl 4-methylthiophene-2-carboxylate Preparation Products

• Methyl 3-methylthiophene-2-carboxylate (81452-54-2)
• Methyl 4-methylthiophene-2-carboxylate (28686-90-0)

• 1. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
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  Chung-Sung Yang,Mong-Shian Shih,Fang-Yi Chang New J. Chem., 2006,30, 729-735
• 4. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 5. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Thiophenes Thiophene carboxylic acids and derivatives

Recent Advances in the Application of Methyl 4-methylthiophene-2-carboxylate (CAS: 28686-90-0) in Chemical Biology and Pharmaceutical Research

Methyl 4-methylthiophene-2-carboxylate (CAS: 28686-90-0) is a heterocyclic compound that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its thiophene ring and ester functional group, serves as a key intermediate in the synthesis of various bioactive molecules. Recent studies have highlighted its potential in drug discovery, particularly in the development of novel therapeutics targeting infectious diseases, cancer, and neurological disorders.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of Methyl 4-methylthiophene-2-carboxylate as a building block for the synthesis of small-molecule inhibitors targeting bacterial efflux pumps. The researchers utilized this compound to develop a series of derivatives that exhibited potent activity against multidrug-resistant Staphylococcus aureus strains. The study underscored the importance of the thiophene scaffold in enhancing the pharmacokinetic properties of these inhibitors, such as improved membrane permeability and metabolic stability.

In the field of oncology, Methyl 4-methylthiophene-2-carboxylate has been employed as a precursor for the synthesis of kinase inhibitors. A recent preprint on bioRxiv detailed the design and evaluation of thiophene-based analogs that selectively target aberrant kinase signaling pathways in glioblastoma. The researchers reported that derivatives of Methyl 4-methylthiophene-2-carboxylate showed promising in vitro and in vivo efficacy, with one candidate advancing to preclinical development. These findings highlight the compound's potential as a scaffold for the development of next-generation anticancer agents.

Beyond its applications in drug discovery, Methyl 4-methylthiophene-2-carboxylate has also been explored in chemical biology as a tool for probing protein-ligand interactions. A 2024 study in ACS Chemical Biology described the use of this compound in the development of photoaffinity probes for mapping the binding sites of G protein-coupled receptors (GPCRs). The researchers demonstrated that the thiophene moiety could be functionalized to incorporate photoreactive groups, enabling the covalent capture of transient receptor-ligand complexes. This approach provides valuable insights into the molecular mechanisms of GPCR activation and could facilitate the design of more selective therapeutics.

Despite these advancements, challenges remain in optimizing the synthetic routes for Methyl 4-methylthiophene-2-carboxylate and its derivatives. A recent review in Organic Process Research & Development discussed the limitations of current methodologies, such as low yields and the generation of hazardous byproducts. The authors proposed alternative catalytic strategies, including the use of transition metal complexes and biocatalysts, to improve the efficiency and sustainability of the synthesis process. These innovations could further enhance the accessibility of this compound for research and industrial applications.

In conclusion, Methyl 4-methylthiophene-2-carboxylate (CAS: 28686-90-0) continues to be a valuable asset in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate and its potential in drug discovery underscore the importance of ongoing investigations into its applications. Future research should focus on addressing the synthetic challenges and expanding the scope of its utility in the development of novel therapeutics and chemical probes.

• 391936-75-7(2-Thiophenecarboxylicacid, 5-formyl-4-methyl-, methyl ester)
• 14300-61-9(Ethyl 4-(hydroxymethyl)thiophene-2-carboxylate)
• 57041-28-8(2-Thiophenecarboxylic acid, 3,5-dimethyl-, methyl ester)
• 81452-54-2(Methyl 3-methylthiophene-2-carboxylate)
• 62404-00-6(2-Thiophenecarboxylic acid, 4-phenyl-, ethyl ester)
• 168850-69-9(Methyl 4,5-dimethylthiophene-2-carboxylate)
• 54796-49-5(4-(methoxymethyl)thiophene-2-carboxylic acid)
• 67808-68-8(2-Thiophenecarboxylic acid, 4-formyl-, methyl ester)
• 6520-81-6(2,4-Thiophenedicarboxylic acid, dimethyl ester)
• 21676-90-4(METHYL 4-PHENYLTHIOPHENE-2-CARBOXYLATE)