4815-32-1

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER is used as a key intermediate in the Gewald synthesis for the production of 2-aminothiophenes. These 2-aminothiophenes are essential building blocks in the development of various pharmaceutical compounds, including those with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER is utilized as a versatile reagent for the synthesis of a wide range of organic compounds. Its unique chemical properties allow for various reactions and transformations, contributing to the advancement of organic chemistry research and development.
Used in Chemical Synthesis:
2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER is also employed in chemical synthesis processes, where it acts as a precursor to other valuable compounds. Its light yellow solid form and chemical properties make it a reliable and efficient starting material for the synthesis of various chemical products.

InChI:InChI=1/C8H11NO2S/c1-3-11-8(10)6-4-5(2)12-7(6)9/h4H,3,9H2,1-2H3

Upstream product

• 123-38-6 propionaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 144918-37-6 1-cyano-1-ethoxycarbonyl-1-butene 
• 123-72-8 butyraldehyde 

Downstream Products

• 38201-63-7 2-Mercapto-6-methyl-thieno<2,3-d>pyrimidin-4(3H)-on 
• 206666-21-9 4-(3,4-dihydro-4-oxo-6-methyl-thieno-[2,3-d]-pyrimidin-2-yl)-benzoic acid methylester 
• 590376-44-6 2-(2-cyano-acetylamino)-5-methyl-thiophene-3-carboxylic acid ethyl ester 
• 890014-20-7 [(6-methylthieno[2,3-d]pyrimidin-4-yl)thio]acetic acid 
• 878699-59-3 2-(chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one 
• 108099-55-4 6-Bromomethyl-4-chlorothieno<2,3-d>pyrimidine 
• 106691-21-8 4-chloro-6-methylthieno<2,3-d>pyrimidine 
• 151258-70-7 N-methyl-N-phenyl 2-(1-pyrrolyl)-5-methylthiophen-3-carboxamide 
• 151258-67-2 2-(1-pyrrolyl)-5-methylthiophen-3-carboxylic acid 
• 158460-90-3 [3-(4-Bromo-2-fluoro-benzyl)-6-(4-methyl-piperazin-1-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-thieno[2,3-d]pyrimidin-1-yl]-acetic acid ethyl ester 
• 158460-89-0 ethyl 3-(4-bromo-2-fluorobenzyl)-2,4-dioxo-6-(morpholin-1-yl)methyl-thieno<2,3-d>pyrimidin-1-acetate 
• 158461-11-1 ethyl 3-(4-bromo-2-fluorobenzyl)-6-bromomethyl-2,4-dioxothieno<2,3-d>pyrimidin-1-acetic acid 
• 122185-96-0 [3-(4-Bromo-2-fluoro-benzyl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-thieno[2,3-d]pyrimidin-1-yl]-acetic acid ethyl ester 
• 122185-75-5 3-(4-Bromo-2-fluoro-benzyl)-6-methyl-1H-thieno[2,3-d]pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis and cytotoxic activity of chalcone analogues containing a thieno[2,3-d]pyrimidin-2-yl group as the A-ring or B-ring

Many natural or synthetic chalcones have potential anti-tumor activity. Here, we synthesized two series of chalcone analogues containing a thieno[2,3-d]pyrimidin-2-yl group and evaluated for their cytotoxic activity towards cultured human lung cancer A549 and colorectal HCT-116 cells. Among them, compound 8d was the most cytotoxic against HCT-116 cells, with an IC50 value of 2.65 μM. Analyses of the phenotypic changes induced by this compound found a dose-dependent accumulation of HCT-116 cells in sub-G1 phase, indicating that compound 8d might induce apoptosis. Furthermore, we found that 8d triggered mitochondrial membrane potential depolarization, promoted reactive oxygen species formation in HCT-116 cells, and increased the percentage of early and late apoptotic cells. Finally, immunoblotting indicated that 8d increased PARP-1 and caspases 3, 7 and 9 cleavage. These data suggest that compound 8d induces apoptosis via the mitochondrial death pathway.

Synthesis of Tetrasubstituted Thiophenes via Direct Metalation

Thiophene moiety can be derivatized by various synthetic procedures. The most convenient method seems to be derivatization via direct metalation, but synthesis of polysubstituted thiophenes bearing reactive groups is difficult because of high reactivity of organometallic reagents. This work reports the preparation of complex heterocyclic compounds using direct metalation of thiophenes with various reagents (Knochel-Hauser bases, LDA) as an efficient synthetic tool.

Chalcone analogue containing thieno[2,3-d]pyrimidine-2-yl, preparation method and uses thereof

The invention discloses a chalcone analogue containing thieno[2,3-d]pyrimidine-2-yl, wherein the chalcone analogue is represented by a general formula (I), and various substituents are defined in thespecification. The invention further discloses a preparation method of the compound. According to the present invention, the compound represented by the general formula (I) has inhibiting effects on the proliferation of human breast cancer cell lines (MFC-7 and MDA-MB-231), human cervical cancer cell lines (HeLa), human colon cancer cell lines (HCT-116 and HT-29) and human lung cancer cell lines (A549), has inhibiting effect on the proliferation of human hepatoma cell lines (HepG2), and can be used as an antitumor drug.

Synthesis, cytotoxic evaluation and target identification of thieno[2,3-d]pyrimidine derivatives with a dithiocarbamate side chain at C2 position

Two series of thieno[2,3-d]pyrimidine derivatives bearing a dithiocarbamate side chain at the C2 position were synthesized and evaluated for cytotoxic activity in human lung cancer A549 and colon cancer HCT-116 cell lines. Compound 3n exhibited the most cytotoxic effect on A549 cells with an IC50 value of 4.87 μM, inducing a cell cycle arrest at G2/M phase and activating the spindle assembly checkpoint (SAC). To identify the target protein(s) of 3n, we incorporated biotin with 3n through a three-carbon chain and an amide bond to synthesize probe 10. The targeted proteins were pulled down from the A549 total cell lysate by biotin-streptavidin affinity purification and analyzed by mass spectrometry. Tubulin was the only protein identified, which is related to the SAC and directly binds to probe 10 both in vivo and in vitro. Furthermore, compound 3n inhibited tubulin polymerization in vitro in a dose-dependent manner, competed with taxol in binding to tubulin, exerting cytotoxic activity toward taxol-resistant A549 cells. These results demonstrate that thieno[2,3-d]pyrimidine derivative 3n exhibits cytotoxicity in cancer cells by targeting tubulin to activate the SAC and potentially acts as a therapeutic lead compound for taxol-resistant cancers.

THIENOPYRIMIDINE DERIVATIVE AND USE THEREOF

The present invention relates to a novel thienopyrimidine derivative and a use thereof, and more particularly, to a novel thienopyrimidine derivative compound and a composition for preventing or treating cancer comprising the same. The compound of the present invention can be effectively used for treating cancer with high FLT3 inhibitory activity and safety. In particular, the compound of the present invention has excellent solubility in physiological salt solutions including water, and thus can be more effectively used for development of therapeutic agents for cancer.COPYRIGHT KIPO 2018

SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS

The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

A green chemical approach: a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents

Abstract: The synergic effect of choline chloride/urea as a deep eutectic solvent was investigated in the synthesis of 2-aminothiophene derivatives via a three-component cyclocondensation of a ketone or an aldehyde with activated nitriles and elemental sulfur catalyzed by NaOH as cheap and highly accessible base. The advantages of this catalytic protocol are eco-friendly, easy to set up, reusability, and a simple separation and purification of products without using chromatography in high yields at short times. Graphical abstract: [Figure not available: see fulltext.]

THIENOPYRIMIDINONE NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided.

Structural modifications at the 6-position of thieno[2,3- d ]pyrimidines and their effects on potency at FLT3 for treatment of acute myeloid leukemia

Fms-like tyrosine kinase 3 (FLT3) is a well-known and important target for the treatment of acute myeloid leukemia (AML). A series of thieno[2,3-d]pyrimidine derivatives from a modification at the 6-position were synthesized to identify effective FLT3 inhibitors. Although compounds 1 and 2 emerged as promising FLT3 inhibitors among the synthesized compounds, both compounds exhibited poor metabolic stability in human and rat liver microsomes. Hence, further optimization was required for the discovery of FLT3 inhibitors, with a focus on improving metabolic stability. Compound 16d, which had structural modifications of the methyl group at the 5-position and the 4-(2-methylaminoethoxy) phenyl group at the 6-position, exhibited good inhibitory activity against FLT3 and showed effective antiproliferative activity against four leukemia cell lines, including MV4-11. Moreover, compound 16d displayed enhanced metabolic stability. The results of this study indicated that 16d could be a promising compound for further optimization and development as a potent FLT3 inhibitor.

Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines

An extension of our previous research work has resulted in a number of new ATP-competitive CK2 inhibitors that have been identified among 4-aminothieno[2,3-d]pyrimidine derivatives. The most active compounds obtained in the course of the research are 3-(5-p-tolyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5e (NHTP23, IC50 = 0.01 μM), 3-(5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5g (NHTP25, IC50 = 0.065 μM) and 3-(6-methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5n (NHTP33, IC50 = 0.008 μM). Structure-activity relationships of the tested 4-aminothieno[2,3-d]pyrimidine derivatives have been studied and their binding mode with ATP-acceptor site of CK2 has been proposed. A negative effect of intramolecular hydrogen bonding in the compounds' structure is discussed.