19369-53-0

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER is used as a starting reagent for the synthesis of Thieno[2,3-b]Pyridinones and 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine derivatives. These compounds are known to act as cytoprotectants, which means they help protect cells from damage caused by various factors, such as oxidative stress or toxins. Additionally, these derivatives also serve as inhibitors of the N-Methyl-D-aspartate (NMDA) receptor, which plays a significant role in the central nervous system and is involved in various neurological disorders.
The application of 2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER in the pharmaceutical industry is primarily due to its ability to contribute to the development of novel therapeutic agents with potential applications in treating neurological conditions and providing cytoprotection. By synthesizing Thieno[2,3-b]Pyridinones and 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine derivatives, researchers can explore their potential as new drugs for the treatment of various diseases and disorders related to the central nervous system.

InChI:InChI=1/C7H9NO2S/c1-4-3-5(6(8)11-4)7(9)10-2/h3H,8H2,1-2H3

Upstream product

• 123-38-6 propionaldehyde 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 76575-28-5 2-methyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid 
• 72242-31-0 5-methyl-2-(2-nitro-anilino)-thiophene-3-carboxylic acid methyl ester 
• 108831-66-9 6-Methylthieno<2,3-d>pyrimid-4-one 

Relevant academic research and scientific papers

Structure-activity relationship of tumor-selective 5-substituted 2-amino-3-carboxymethylthiophene derivatives

Methyl-2-amino-5-[2-(4-methoxyphenethyl)]thiophene-3-carboxylate (8c) is the prototype of a well-defined class of tumorselective agents. Compound 8c preferentially inhibited the proliferation of a number of tumor cell lines including many human T-lymphoma/leukemia cells, but also several prostate, renal, central nervous system and liver tumor cell types. Instead, a broad variety of other tumor cell lines including B-lymphomas and HeLa cells were not affected. The tumor selectivity (TS; selectivity index or preferential suppression of CEM lymphoma (IC50=0.90 mm) versus HeLa tumor cell carcinoma (IC50=39 mm)) amounted up to ～43 for 8c. At higher concentrations, the compound proved cytotoxic rather than cytostatic. The antiproliferative potency and selectivity of 8c could be preserved by replacing the ethyl linker between the 2-amino- 3-carboxymethylthiophene and the substituted aryl by a thioalkyl but not by an oxyalkyl nor an aminoalkyl. Among >50 novel 8c derivatives, the 5-(4-ethyl- and 4-isopropylarylmethylthio) thiophene analogues, methyl-2-amino-5-((4-ethylphenylthio) methyl)thiophene-3-carboxylate (13m) and methyl-2- amino-5-((4-isopropylphenylthio)methyl)thiophene-3-carboxylate (13n), were more potent (IC50 : 0.3-0.4 mm) and selective (TS: 100-144) anti-T-lymphoma/leukemia agents than the prototype compound.

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.

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands

Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.

Pronounced anti-proliferative activity and tumor cell selectivity of 5-alkyl-2-amino-3-methylcarboxylate thiophenes

5-(2-(4-Methoxyphenyl)ethyl)-2-amino-3-methylcarboxylate thiophene (TR560) is the prototype drug of a recently discovered novel class of tumor-selective compounds that preferentially inhibit the proliferation of specific tumor cell types (e.g. leukemia/lymphoma). Here, we further increased tumor selectivity by simplification of the molecule through replacing the 4-methoxyphenyl moiety by an alkyl chain. Several 2-amino-3-methylcarboxylate thiophene derivatives containing at C-5 an alkyl group consisting of at least 6 (hexyl) to 9 (nonyl) carbon units showed pronounced anti-proliferative activity in the mid-nanomolar range with 500- to 1000-fold tumor cell selectivity. The compounds preferentially inhibited the proliferation of T-lymphoma CEM and Molt/4, prostate PC-3, kidney Caki-1 and hepatoma Huh-7 tumor cells, but were virtually inactive against other tumor cell lines including B-lymphoma Raji and cervix carcinoma HeLa cells. The novel prototype drug 3j (containing a 5-heptyl chain) elicited a cytotoxic, rather than cytostatic activity, already after 4?h of exposure. The unusual tumor selectivity could not be explained by a differential uptake (or efflux) of the drug by sensitive versus resistant tumor cells. Exposure of a fluorescent derivative of 3j revealed pronounced uptake of the drug in the cytoplasm, no visible appearance in the nucleus, and a predominant localization in the endoplasmic reticulum. These observations may be helpful to narrow down the intracellular localization and identification of the molecular target of the 5-substituted thiophene derivatives.

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.

NOVEL ANTI-CANCER COMPOUNDS

The present invention relates to compounds having cytostatic activity against tumor cells. The compounds of the invention are of formula (I), or derivatives hereof, wherein R0, R1, R2, A, and X have defined meanings as described in claim 1.

NOVEL ANTI-CANCER COMPOUNDS

The present invention relates to compounds having cytostatic activity against tumor cells. The compounds of the invention are of formula (I), or derivatives hereof, wherein R0, R1, R2, A, and X have defined meanings as described in claim 1.

Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of Cyclin D1-CDK4: Synthesis, biological evaluation, and structure-activity relationships

The synthesis and evaluation of new analogues of thieno[2,3-d]pyrimidin-4-yl hydrazones are described. 2-Pyrdinecarboxaldehyde [6-(tert-butyl)thieno[2,3-d]pyrimidine-4-yl]hydrazone derivatives have been identified as cyclin-dependent kinase 4 (CDK4) inhibitors. The potency, selectivity profile, and structure-activity relationship of this series of compounds are discussed.

Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds

The compounds of formula I herein exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, for treating a patient suffering from, or subject to, a physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

METHODS OF TREATMENT USING A THIENO-BENZODIAZEPINE

2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno-[2,3-b][1, 5] benzodiazepine, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of disorders of the central nervous system. The compound has the following structure: STR1