134690-40-7

Basic information

• Product Name: Benzenamine, 3-ethynyl-4-methyl- (9CI)
• Synonyms: Benzenamine, 3-ethynyl-4-methyl- (9CI);2-Ethynyl-4-aMinotoluene;3-Ethynyl-4-Methyl-benzenaMine
• CAS NO: 134690-40-7
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17446
• Product Categories: Amines;Aromatics;Intermediates;Amines, Aromatics, Intermediates
• Mol File: 134690-40-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Benzenamine, 3-ethynyl-4-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 3-ethynyl-4-methyl- (9CI)(134690-40-7)
• EPA Substance Registry System: Benzenamine, 3-ethynyl-4-methyl- (9CI)(134690-40-7)

Safety Data

• Hazardous Substances Data: 134690-40-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzenamine, 3-ethynyl-4-methyl(9CI) is used as an intermediate in the synthesis of various pyrimidine derivatives, which are essential in the development of pharmaceutical compounds. Its unique structure allows for the creation of a wide range of molecules with potential applications in the treatment of various diseases and conditions.
Used in Chemical Research:
As a versatile organic compound, Benzenamine, 3-ethynyl-4-methyl(9CI) is also utilized in chemical research for the exploration of new reactions and the development of novel synthetic pathways. Its ethynyl and amino groups provide opportunities for further functionalization and modification, making it a valuable building block in the synthesis of complex organic molecules.

Upstream product

• 7745-92-8 2-iodo-1-methyl-4-nitrobenzene 
• 35944-64-0 3-iodo-4-methylaniline 
• 1303946-47-5 3-trimethylsilylethynyl-4-methylaniline 
• 905439-45-4 4-(5-amino-2-methyl-phenyl)-2-methyl-but-3-yn-2-ol 

Downstream Products

• 1378976-11-4 4-methyl-3-(1H-1,2,3-triazol-4-yl)aniline 

Relevant articles and documents

3-ACETYLENYL-PYRAZOLE-PYRIMIDINE DERIVATIVE, AND PREPARATION METHOD THEREFOR AND USES THEREOF

The present invention relates to the field of chemical and medicine, more particularly, 3-ethynylpyrazolopyrimidine derivatives and their preparation methods and uses. The invention provides a 3-ethynylpyrazolopyrimidine derivative, and the structure is shown in formula I. The present invention also provides preparation methods and use of 3-ethynylpyrazolopyrimidine derivatives, comprising the compounds and derivatives, and their pharmaceutical compositions for the use of the treatment and prevention of tumors.

From Lead to Drug Candidate: Optimization of 3-(Phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Derivatives as Agents for the Treatment of Triple Negative Breast Cancer

Herein we report the sophisticated process of structural optimization toward a previously disclosed Src inhibitor, compound 1, which showed high potency in the treatment of triple negative breast cancer (TNBC) both in vitro and in vivo but had considerable toxicity. A series of 3-(phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives were synthesized. In vitro cell-based phenotypic screening together with in vivo assays and structure-activity relationship (SAR) studies finally led to the discovery of N-(3-((4-amino-1-(trans-4-hydroxycyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)ethynyl)-4-methylphenyl)-4-methyl-3-(trifluoromethyl)benzamide (13an). 13an is a multikinase inhibitor, which potently inhibited Src (IC50 = 0.003 μM), KDR (IC50 = 0.032 μM), and several kinases involved in the MAPK signal transduction. This compound showed potent anti-TNBC activities both in vitro and in vivo, and good pharmacokinetic properties and low toxicity. Mechanisms of action of anti-TNBC were also investigated. Collectively, the data obtained in this study indicate that 13an could be a promising drug candidate for the treatment of TNBC and hence merits further studies.

Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition

Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.

Aminopyrimidine Derivatives With Tie2 Inhibiting Activity

The invention relates to a compound of the Formula I or salt thereof wherein Rx, Ry, Rx, R5, R6, A, B, L, n and m are as defined in the description. The invention also relates to pharmaceutical compositions of said compounds, the use of said compounds as medicaments and in the production of an anti-angiogenic effect in a warm blooded animal. The invention also relates to processes for the preparation of said compounds.

PYRIMIDINE COMPOUNDS HAVING TIES (TEK) INHIBITORY ACTIVITY

The invention relates to a compound of the Formula (I) or salt thereof wherein Rx, Ry, Rz, R5, R6, A, B, L, n and m are as defined in the description. The invention also relates to pharmaceutical compositions of said compounds, the use of said compounds as medicaments and in the production of an anti-angiogenic effect in a warm blooded animal. The invention also relates to processes for the preparation of said compounds.