53562-51-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-3-thiophenecarboxylic acid methyl ester is used as a building block in the synthesis of various pharmaceuticals due to its unique chemical structure and reactivity. It contributes to the development of new drugs by providing a versatile starting material for medicinal chemists.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Methyl-3-thiophenecarboxylic acid methyl ester serves as an intermediate for the preparation of various agrochemicals. Its properties make it suitable for the synthesis of compounds with pesticidal or herbicidal activity, enhancing crop protection and yield.
Used in Dye Production:
2-Methyl-3-thiophenecarboxylic acid methyl ester is utilized as an intermediate in the production of dyes. Its chemical properties allow for the creation of a range of colorants used in various industries, including textiles, plastics, and printing inks.
Used in Fragrance Industry:
2-Methyl-3-thiophenecarboxylic acid methyl ester is also employed in the fragrance industry as an intermediate for synthesizing scented compounds. Its strong, fruity odor makes it a valuable component in creating complex and appealing fragrances for perfumes, cosmetics, and other scented products.
Used in Flavorings Industry:
2-Methyl-3-thiophenecarboxylic acid methyl ester is used in the flavorings industry to develop taste enhancers and additives for food and beverages. Its fruity notes contribute to the creation of flavors that can improve the taste profiles of various consumer products.

InChI:InChI=1/C7H8O2S/c1-5-6(3-4-10-5)7(8)9-2/h3-4H,1-2H3

Upstream product

• 1918-78-1 2-methylthiophene-3-carboxylic acid 
• 74-88-4 methyl iodide 
• 40018-26-6 1,4-dithiane-2,5-diol 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 88-13-1 3-Thiophene carboxylic acid 
• 67-56-1 methanol 

Downstream Products

• 88048-78-6 methyl 2-(bromomethyl)thiophene-3-carboxylate 
• 148564-47-0 milfasartan 
• 172292-52-3 2-[4-Butyl-5-(2'-cyano-biphenyl-4-ylmethyl)-2-methyl-6-oxo-6H-pyrimidin-1-ylmethyl]-thiophene-3-carboxylic acid methyl ester 
• 148564-34-5 methyl 2-<<4-butyl-2-methyl-6-oxo-5-<<2'-<1-(triphenylmethyl)-1H-tetrazol-5-yl><1,1'-biphenyl>-4-yl>methyl>-1(6H)-pyrimidinyl>methyl>-3-thiophenecarboxylate 
• 1334598-73-0 C₁₃H₁₂O₄S₂ 
• 1334598-77-4 C₁₃H₁₁NO₃S 
• 1259396-11-6 methyl 5-bromo-2-methylthiophene-3-carboxylate 
• 1334598-41-2 C₁₅H₁₄O₃S 
• 1334598-50-3 C₁₄H₁₄O₄S₂ 
• 1334598-54-7 C₁₄H₁₃NO₃S 
• 1334598-01-4 C₂₀H₁₈N₂O₂S₂ 
• 1334598-04-7 C₂₁H₂₀N₂O₂S₂ 
• 1334598-15-0 C₁₉H₁₅N₃O₂S 
• 1334598-18-3 C₁₉H₁₈N₂O₃S₃ 

Relevant academic research and scientific papers

The synthesis of four isomeric bisthienothiepinones

The displacement reaction between sodium thiophene-3-thiolate and methyl 3-(bromomethyl)thiophene-2-carboxylate (5) gave the expected thioether 7a. Basic hydrolysis afforded the carboxylic acid 7b; conversion to the acid chloride, and treatment of the latter with stannic chloride then produced the bisthienothiepinone 1. Using analogous reactions the isomers 2-4 were also synthesized.

Aromatic heterocyclic lactam compound as well as preparation method and application thereof

The invention discloses an aromatic heterocyclic lactam compound as well as a preparation method and an application thereof. The invention particularly discloses an aromatic heterocyclic lactam compound shown as a formula (I), or pharmaceutically acceptable salt thereof, or an enantiomer, a diastereoisomer, a tautomer, a solvate, a polymorphic substance or a prodrug thereof, a preparation method of the aromatic heterocyclic lactam compound and an application of the aromatic heterocyclic lactam compound to pharmacy.

Discovery of a potent glucokinase activator with a favorable liver and pancreas distribution pattern for the treatment of type 2 diabetes mellitus

Glucokinase (GK) is an enzyme that plays an important role as a glucose sensor while maintaining whole body glucose homeostasis. Allosteric activators of GK (GKAs) have the potential to treat type 2 diabetes mellitus. To identify novel GKAs, a series of compounds based on a thiophenyl-pyrrolidine scaffold were designed and synthesized. In this series, compound 38 was found to inhibit glucose excursion in an oral glucose tolerance test (OGTT) in mice. Optimization of 38 using a zwitterion approach led to the identification of the novel GKA 59. GKA 59 exhibited potent blood glucose control in the OGTT test as well as a favorable safety profile. Owing to low pancreatic distribution, compound 59 primarily activates GK in the liver. This characteristic could overcome limitations of other GKAs, such as hypoglycemia, increased plasma triglycerides, and loss of efficacy.

Design, synthesis, and structure-activity relationship studies of novel thienopyrrolidone derivatives with strong antifungal activity against Aspergillus fumigates

In order to further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compounds (I), two series of novel azoles featuring thieno[2,3-c]pyrrolidone and thieno[3,2-c]pyrrolidone nuclei were designed and evaluated for their in vitro activity on the basis of the binding mode of albaconazole using molecular docking, along with SARs of antifungal triazoles. Most of target compounds exhibited excellent activity against Candida and Cryptococcus spp., with MIC values in the range of 0.0625 μg/ml to 0.0156 μg/ml. The thieno[3,2-c]pyrrolidone unit was more suited for improving activity against Aspergillus spp. The most potent compound, 18a, was selected for further development due to its significant in vitro activity against Aspergillus spp. (MIC Combining double low line 0.25 μg/ml), as well as its high metabolic stability in human liver microsomes.

NOVEL THIOPHENECARBOXAMIDE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

The object of the present invention is to provide a compound having a glucokinase-activating effect. A pharmaceutical composition comprising a compound represented by the general formula (I) or a pharmaceutically acceptable salt thereof as an active ingredient: wherein X means a nitrogen atom or CR6, wherein R6 means a hydrogen atom or a halogen atom; R1 means a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C6 alkylthio group; R2 means a hydrogen atom or a fluorine atom; R3 means a hydrogen atom or a C1-C6 alkyl group; and one of R4 and R5 means a hydrogen atom or a C1-C6 alkyl group, and the other means a C1-C6 alkylenecarboxylic acid, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, or CONH2.

Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high s

A novel class of compounds: Synthesis of 5,5′-carbonyl-bis(5,6- dihydro-4H-furo- and thieno-[2,3-c]pyrrol-4-ones)

We hereby report the first synthesis of novel class of compounds, 5,5′-carbonyl-bis(5,6-dihydro-4H-thieno- and furo-[2,3-c]pyrrol-4-one starting from methyl 2-(2-methoxy-2-oxoethyl) thiophene- and furan-3-carboxylate, respectively. The ester functionalities connected to methylene group were regiospecifically converted to the desired monoacyl azides. Curtius rearrangement of acyl azides followed by hydrolysis of the formed isocyanates gave the symmetrical urea derivatives. Cyclization of the ester groups provided the target compounds.

N-3-Substituted Pyrimidones as Potent, Orally Active, AT1 Selective Angiotensin II Receptor Antagonists

A novel series of nonpeptide angiotensin II (A II) antagonists containing a pyrimidinone ring which carries a C-linked biphenyltetrazole moiety and a carboxyheteroaryl group on the 3-position have been prepared.Their affinity for the AT1 receptor was determined in a binding assay on rat adrenal cortical membranes.The in vivo antihypertensive properties were tested by evaluating the inhibition of the pressor response to A II followed by iv and id administration.Extensive molecular modeling studies, including comparison of molecular electrostatic potential distributions, conformational analysis, and overlays on a computational pharmacophore model of A II, were used to evaluate structural parameters of the new compounds, in comparison to other known A II antagonists (e.g., DUP-753 and SKandF 108566).According to the modeling studies, the introduction of a (carboxyheteroaryl)methyl moiety at the 3-position of the pyrimidinone ring led to derivatives with increased potency.Methyl 2-methyl>-1-(6H)-pyrimidinyl>methyl>-3-thiophenecarboxylate (3k, LR-B/081), one of the most potent compounds in the series (Ki = 1.4 nM), exhibited a marked antihypertensive activity on oral administration to conscious renal hypertensive rats, with long duration of action.It was selected for clinical evaluation in the treatment of hypertension in man.

Phenyl or heteroaryl and tetrahydronaphthyl substituted diene compounds having retinoid like biological activity

Compounds of Formula 1 STR1 wherein m is 1-4; R 1 --R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R 5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R 6 is hydrogen, lower alkyl, Cl, Br, I, OR 11, SR 11, OCOR 11, SCOR 11, NH2, NHR 11, N(R 11) 2, NHCOR 11 OR NR 11 --COR 11 ; R 20 is independently hydrogen or lower alkyl; Y is an aromatic group such as phenyl or naphthyl, or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; A is (CH 2) n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8, CONR 9 R 10, --CH 2 OH, CH 2 OR 11, CH 2 OCOR 11, CHO, CH(OR 12) 2, CHOR 13 O, --COR 7, CR 7 (OR 12) 2, or CR 7 OR 13 O, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower aklylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, have retinoid like biological activity. In the compounds of the invention the A-B and the butadiene groups are attached to adjacent aromatic carbons of the Y moiety.