145679-40-9

Basic information

• Product Name: (R)-5-(oxiran-2-ylmethoxy)quinoline
• Synonyms: (R)-5-(oxiran-2-ylmethoxy)quinoline;(R)-5-OxiranylMethoxyquinoline;(R)-5-(oxiranylMethoxy)-quinoline, 5-[(2R)-oxiranylMethoxy]-quinoline, (2R)-1-(5-quinolinyloxy)-2,3-epoxypropane;5-[(2R)-2-OxiranylMethoxy]-quinoline
• CAS NO: 145679-40-9
• Molecular Formula: C12H11NO2
• Molecular Weight: 201.22124
• Product Categories: Aromatics;Heterocycles
• Mol File: 145679-40-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 361.394°C at 760 mmHg
• Flash Point: 131.845°C
• Appearance: /
• Density: 1.249g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: (R)-5-(oxiran-2-ylmethoxy)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-(oxiran-2-ylmethoxy)quinoline(145679-40-9)
• EPA Substance Registry System: (R)-5-(oxiran-2-ylmethoxy)quinoline(145679-40-9)

Safety Data

• Hazardous Substances Data: 145679-40-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

(R)-5-(oxiran-2-ylmethoxy)quinoline can be used in the preparation of piperidine derivatives.

InChI:InChI=1/C12H11NO2/c1-4-11-10(3-2-6-13-11)12(5-1)15-8-9-7-14-9/h1-6,9H,7-8H2/t9-/m1/s1

Upstream product

• 578-67-6 quinolin-5-ol 
• 115314-14-2 (R)-glycidyl nosylate 
• 86132-70-9 (2R)-3-(2-nitrobenzenesulfonyloxy)-1,2-epoxypropane 

Downstream Products

• 1416053-66-1 (2R)-1-[4-(diphenylamino)piperidin-1-yl]-3-(quinolin-5-yloxy)propan-2-ol 
• 1416053-68-3 (2R)-1-{4-[bis(4-methylphenyl)amino]piperidin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol 
• 1416053-69-4 (2R)-1-{4-[bis(4-fluorophenyl)amino]piperidin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol 
• 1416053-77-4 (2R)-1-{(2R,3R)-2,3-diphenyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl}-3-(quinolin-5-yloxy)propan-2-ol 
• 1416053-79-6 (2R)-1-[5,6-diphenylspiro(1,3-benzodioxole-2,4'-piperidine)-1'-yl]-3-(quinoline-5-yloxy)propan-2-ol 
• 414867-42-8 N-{1-[2-(R)-hydroxy-3-(quinolin-5-yloxy)-propyl]-piperidine-4-carbonyl}-3-(3-pyridyl)-alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide 
• 1026330-33-5 5-phenyl-2-(3-phenyl-propyl)-pentanoic acid {1-[2-hydroxy-3-(quinolin-5-yloxy)-propyl]-piperidin-4-yl}-amide 
• 167465-36-3 zosuquidar trihydrochloride 

Relevant articles and documents

Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance

The inhibition of ABC (ATP binding cassette) transporters is considered a powerful tool to reverse multidrug resistance. Zosuquidar featuring a difluorocyclopropyl-annulated dibenzosuberyl moiety has been found to be an inhibitor of the P-glycoprotein, one of the best-studied multidrug efflux pumps. Twelve 5-oxyisoquinoline derivatives, which are analogues of zosuquidar wherein the dibenzosuberyl-piperazine moiety is replaced by either a diarylaminopiperidine or a piperidone-derived acetal or thioacetal group, have been synthesized as pure enantiomers. Their inhibitory power has been evaluated for the bacterial multidrugresistance ABC transporter LmrCD and fungal Pdr5. Four of the newly synthesized compounds reduced the transport activity to a higher degree than zosuquidar, being up to fourfold more efficient than the lead compound in the case of LmrCD and about two times better for Pdr5.

Process for preparing 10,11-methanobenzosuberane derivatives

This invention provides a process to prepare 10,11-(optionally substituted)methanodibenzosuberane derivatives. The invention also provides an intermediate in this process.

10,11-Methanodibenzosuberane derivatives

10,11-Methanodibenzosuberane derivatives, i.e., the compounds of Formula I: STR1 wherein: A is --CH2 --CH2 --, --CH2 --CHRa --CH2 --, or --CH2 --CHRa --CHRb --CH2 --, where one of Ra or Rb is H, OH, or lower acyloxy, and the other is H; R1 is H, F, Cl or Br; R2 is H, F, Cl or Br; and R3 is heteroaryl or phenyl optionally substituted with F, Cl, Br, CF3, CN, NO2 or OCHF2 ; and the pharmaceutically acceptable salts thereof, are useful chemosensitizing agents, e.g., for cancer chemotherapy, particularly for treating multidrug resistance.