145679-40-9

Usage

Uses

Used in Pharmaceutical Industry:
(R)-5-(oxiran-2-ylmethoxy)quinoline is used as a synthetic intermediate for the preparation of various piperidine derivatives. These derivatives are often found in the development of pharmaceutical compounds due to their diverse biological activities and potential therapeutic applications.
Used in Chemical Synthesis:
As a chiral building block, (R)-5-(oxiran-2-ylmethoxy)quinoline is used as a key component in the synthesis of more complex organic molecules, particularly those with potential applications in the pharmaceutical, agrochemical, and material science industries. Its unique structural features allow for selective reactions and the creation of novel compounds with specific properties.
Used in Research and Development:
In academic and industrial research settings, (R)-5-(oxiran-2-ylmethoxy)quinoline serves as a valuable compound for exploring new reaction pathways, understanding stereochemistry, and developing innovative synthetic methods. Its use in research can lead to the discovery of new drugs, materials, or chemical processes.

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 
• 86132-70-9 (2R)-3-(2-nitrobenzenesulfonyloxy)-1,2-epoxypropane 
• 115314-14-2 (R)-glycidyl nosylate 

Downstream Products

• 1026330-33-5 5-phenyl-2-(3-phenyl-propyl)-pentanoic acid {1-[2-hydroxy-3-(quinolin-5-yloxy)-propyl]-piperidin-4-yl}-amide 
• 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 
• 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 
• 167465-36-3 zosuquidar trihydrochloride 

Relevant academic research and scientific papers

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.

Stereochemistry of C-6 nucleophilic displacements on 1,1- difluorocyclopropyldibenzosuberanyl substrates. An improved synthesis of multidrug resistance modulator LY335979 trihydrochloride

Studies of the displacement chemistry of 1,1- difluorocyclopropyldibenzosuberanyl alcohol 4 and its activated bromide derivative 6 have led to an improved approach to anti-2, a key precursor to LY335979 3HCl (1). Bromination of either syn-4 or anti-4 gave

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.

Process for preparing a 10,11-methanodibenzosuberane derivative

This invention provides a process to prepare (2R)-anti-5-{3-[4-(10,11-difluoromethanodibenzosuber-5-yl)piperazin-1-yl]-2-hydroxypropoxy}quinoline.

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.