658084-80-1

Basic information

• Product Name: ETHYL 4-CHLORO-5-ISOPROPYLPYRROLO[2,1-F][1,2,4]TRIAZINE-6-CARBOXYLATE
• Synonyms: ETHYL 4-CHLORO-5-ISOPROPYLPYRROLO[2,1-F][1,2,4]TRIAZINE-6-CARBOXYLATE;Ethyl 4-chloro-5-isopropy...;Ethyl 4-chloro-5-isopropylpyrrolo[1,2-f][1,2,4]triazine-6-carboxylate;ethyl 4-chloro-5-(propan-2-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate
• CAS NO: 658084-80-1
• Molecular Formula: C₁₂H₁₄ClN₃O₂
• Molecular Weight: 267.715
• Mol File: 658084-80-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 4-CHLORO-5-ISOPROPYLPYRROLO[2,1-F][1,2,4]TRIAZINE-6-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-CHLORO-5-ISOPROPYLPYRROLO[2,1-F][1,2,4]TRIAZINE-6-CARBOXYLATE(658084-80-1)
• EPA Substance Registry System: ETHYL 4-CHLORO-5-ISOPROPYLPYRROLO[2,1-F][1,2,4]TRIAZINE-6-CARBOXYLATE(658084-80-1)

Safety Data

• Hazardous Substances Data: 658084-80-1(Hazardous Substances Data)

Usage

General Description

Ethyl 4-chloro-5-isopropylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate is a chemical compound containing an ethyl ester functional group and a pyrrolo triazine ring structure. The presence of a chlorine and an isopropyl group on the pyrrolo triazine ring contributes to its unique chemical properties. This chemical is commonly used in pharmaceutical research and development, as it has potential therapeutic applications. Its molecular structure and functional groups make it suitable for interaction with biological systems and can be studied for its pharmacological effects. The compound's chemical properties and potential pharmacological activity make it an important molecule in drug discovery and development.

Upstream product

• 651744-40-0 ethyl 5-isopropyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-carboxylate 
• 651744-40-0 5-(1-methylethyl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one-6-carboxylic acid ethyl ester 
• 15790-86-0 ethyl-4-methyl-2-(E)-penteneoate 
• 104398-21-2 ethyl 4-(propan-2-yl)-1H-pyrrole-3-carboxylate 
• 2999-46-4 Ethyl isocyanoacetate 
• 651744-39-7 diethyl 1-amino-3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate 
• 651744-38-6 diethyl 3-(propan-2-yl)-1H-pyrrole-2,4-dicarboxylate 

Downstream Products

• 1005196-70-2 C₂₁H₂₅N₅O₄ 

Relevant articles and documents

Synthesis and SAR of 4-(3-hydroxyphenylamino)pyrrolo[2,1-f][1,2,4]triazine based VEGFR-2 kinase inhibitors

A versatile synthesis of the suitably functionalized pyrrolo[2,1-f][1,2,4] triazine nucleus is described. SAR at the C-5 and C-6 positions of the 4-(3-hydroxy-4-methylphenylamino)pyrrolo[2,1-f][1,2,4]triazine template led to compounds with good in vitro potency against VEGFR-2 kinase. Glucuronidation of the phenol group is mitigated by incorporation of a basic amino group on the C-6 side chain of the pyrrolotriazine nucleus.

Design, synthesis, and evaluation of orally active 4-(2,4-difluoro-5- (methoxycarbamoyl)phenylamino)pyrrolo[2,1-f][1,2,4]triazines as dual vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 inhibitors

A series of substituted 4-(2,4-difluoro-5-(methoxycarbamoyl)phenylamino) pyrrolo[2,1-f][1,2,4]-triazines was identified as potent and selective inhibitors of the tyrosine kinase activity of the growth factor receptors VEGFR-2 (Flk-1, KDR) and FGFR-1. The enzyme kinetics associated with the VEGFR-2 inhibition of compound 50 (Ki = 52 ± 3 nM) confirmed that the pyrrolo-[2,1-f][1,2,4]triazine analogues are competitive with ATP. Several analogues demonstrated low-nanomolar inhibition of VEGF- and FGF-dependent human umbilical vein endothelial cell (HUVEC) proliferation. Replacement of the C6-ester substituent of the pyrrolo[2,1-f][1,2,4]-triazine core with heterocyclic bioisosteres, such as substituted 1,3,5-oxadiazoles, afforded compounds with excellent oral bioavailability in mice (i.e., 50 Fpo = 79%). Significant antitumor efficacy was observed with compounds 44, 49, and 50 against established L2987 human lung carcinoma xenografts implanted in athymic mice. A full account of the synthesis, structure-activity relationships, pharmacology, and pharmacokinetic properties of analogues within the series is presented.