130495-08-8

Basic information

• Product Name: 5-(Chloromethyl)-3-bromoisoxazole
• Synonyms: 5-(Chloromethyl)-3-bromoisoxazole;1-Pyrrolidinecarboxylic acid, 2-ethynyl-, 1,1-dimethylethyl ester, (2S)-;(S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate;(S)-1-Boc-2-Ethynylpyrrolidine;(2S)-1-Pyrrolidinecarboxylic acid 2-ethynyl-1,1-diMethylethyl ester;(S)-N-tert-Butoxycarbonyl-2-ethynylpyrrolidine;tert-Butyl (S)-2-ethynylpyrrolidine-1-carboxylate;(S)-N-BOC-2-ETHYNYLPYRROLIDINE
• CAS NO: 130495-08-8
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 196.42972
• Mol File: 130495-08-8.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 249℃
• Flash Point: 104℃
• Appearance: /
• Density: 1.04
• Vapor Pressure: 0.023mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-(Chloromethyl)-3-bromoisoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(Chloromethyl)-3-bromoisoxazole(130495-08-8)
• EPA Substance Registry System: 5-(Chloromethyl)-3-bromoisoxazole(130495-08-8)

Safety Data

• Hazardous Substances Data: 130495-08-8(Hazardous Substances Data)

Usage

General Description

5-(Chloromethyl)-3-bromoisoxazole is a chemical compound with the molecular formula C6H4BrClNO. It is a derivative of isoxazole, a five-membered heterocyclic compound containing an oxygen and nitrogen atom in the ring. The presence of a chloromethyl group and a bromine atom in the structure makes it a potentially reactive compound, capable of participating in various chemical reactions. It is commonly used as a building block in organic synthesis for the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, it can be a useful intermediate in the development of new materials and bioactive compounds. Due to its potential reactivity and versatility, 5-(Chloromethyl)-3-bromoisoxazole has garnered interest in the fields of medicinal chemistry and chemical research.

InChI:InChI=1/C11H17NO2/c1-5-9-7-6-8-12(9)10(13)14-11(2,3)4/h1,9H,6-8H2,2-4H3/t9-/m1/s1

Upstream product

• 109-72-8 n-butyllithium 
• 130419-38-4 (S)-2-(2,2-dibromoethenyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 
• 558-13-4 carbon tetrabromide 
• 69610-41-9 Boc-L-Pro-H 
• 27491-70-9 dimethyl diazomethylphosphonate 
• 21047-57-4 diethyl (1-diazo-2-oxopropyl)phosphonate 
• 147-85-3 L-proline 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 1201915-86-7 (S)-2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1445590-37-3 (S)-tert-butyl 2-(1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylate 
• 147402-53-7 (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole 
• 147402-52-6 A 79814 
• 881691-88-9 tert-butyl (S)-1-(4-(benzyloxy)benzyl)-2-((S)-2-ethynylpyrrolidin-1-yl)-2-oxoethylcarbamate 
• 922529-24-6 ethyl 4-[2-[(2S)-pyrrolidinyl]ethynyl]phenylacetate 
• 922529-40-6 ethyl 4-[2-[1-(tert-butoxycarbonyl)-(2S)-pyrrolidinyl]ethynyl]phenylacetate 

Relevant articles and documents

POTENT HUMAN NEURONAL NITRIC OXIDE SYNTHASE INHIBITORS

Disclosed are 2-aminopyridine derivative compounds for use as inhibitors of nitric oxide synthase (NOS). In particular, the field of the invention relates to 2-aminopyridine derivative compounds for use as inhibitors of neuronal nitric oxide synthase (nNOS), which are formulated as pharmaceutical compositions for treating diseases and disorders associated with nNOS such as Alzheimer's, Parkinson's, and Huntington's diseases, and amytrophic lateral sclerosis, cerebral palsy, stroke/ischemic brain damage, and migraine headaches.

Optimization of Blood-Brain Barrier Permeability with Potent and Selective Human Neuronal Nitric Oxide Synthase Inhibitors Having a 2-Aminopyridine Scaffold

Effective delivery of therapeutic drugs into the human brain is one of the most challenging tasks in central nervous system drug development because of the blood-brain barrier (BBB). To overcome the BBB, both passive permeability and efflux transporter liability of a compound must be addressed. Herein, we report our optimization related to BBB penetration of neuronal nitric oxide synthase (nNOS) inhibitors toward the development of new drugs for neurodegenerative diseases. Various approaches, including enhancing lipophilicity and rigidity of new inhibitors and modulating the pKa of amino groups, have been employed. In addition to determining inhibitor potency and selectivity, crystal structures of most newly designed compounds complexed to various nitric oxide synthase isoforms have been determined. We have discovered a new analogue (21), which exhibits not only excellent potency (Ki 30 nM) in nNOS inhibition but also a significantly low P-glycoprotein and breast-cancer-resistant protein substrate liability as indicated by an efflux ratio of 0.8 in the Caco-2 bidirectional assay.

Series of Alkynyl-Substituted Thienopyrimidines as Inhibitors of Protozoan Parasite Proliferation

Discovery of new chemotherapeutic lead agents can be accelerated by optimizing chemotypes proven to be effective in other diseases to act against parasites. One such medicinal chemistry campaign has focused on optimizing the anilinoquinazoline drug lapatinib (1) and the alkynyl thieno[3,2-d]pyrimidine hit GW837016X (NEU-391, 3) into leads for antitrypanosome drugs. We now report the structure-activity relationship studies of 3 and its analogs against Trypanosoma brucei, which causes human African trypanosomiasis (HAT). The series was also tested against Trypanosoma cruzi, Leishmania major, and Plasmodium falciparum. In each case, potent antiparasitic hits with acceptable toxicity margins over mammalian HepG2 and NIH3T3 cell lines were identified. In a mouse model of HAT, 3 extended life of treated mice by 50%, compared to untreated controls. At the cellular level, 3 inhibited mitosis and cytokinesis in T. brucei. Thus, the alkynylthieno[3,2-d]pyrimidine chemotype is an advanced hit worthy of further optimization as a potential chemotherapeutic agent for HAT.