913000-15-4

Basic information

• Product Name: (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone
• Synonyms: (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone
• CAS NO: 913000-15-4
• Molecular Weight: 514.418
• Mol File: 913000-15-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone(913000-15-4)
• EPA Substance Registry System: (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone(913000-15-4)

Safety Data

• Hazardous Substances Data: 913000-15-4(Hazardous Substances Data)

Usage

Description

(2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone is a heterocyclic compound that features a benzene ring with two benzyloxy groups and a bromine atom, as well as a dihydroisoindol-2-yl group connected to a methanone moiety. This complex structure positions it as a potential pharmaceutical intermediate, valuable in the fields of medicinal chemistry and drug discovery.

Uses

Used in Pharmaceutical Industry:
(2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone serves as a pharmaceutical intermediate, playing a crucial role in the synthesis of various pharmaceutical compounds. Its unique structure may contribute to the development of new drugs with distinct biological activities.
Used in Medicinal Chemistry:
In the realm of medicinal chemistry, (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone is utilized for its potential to exhibit biological activities. Researchers may explore its properties to advance drug discovery and design, possibly leading to the creation of innovative therapeutic agents.
The specific applications and biological activities of (2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone would require further investigation and testing to fully understand its potential and safety in various settings.

Upstream product

• 958253-44-6 methyl 2,4-bis(benzyloxy)-5-bromobenzoate 
• 98437-43-5 methyl 2-chloro-3,4-dihydroxybenzoate 
• 7355-22-8 5-bromo-4-hydroxysalicylic acid 
• 89-86-1 4-hydroxysalicylic acid 
• 496-12-8 isoindoline 
• 912545-10-9 2,4-bis(benzyloxy)-5-bromobenzoic acid 

Downstream Products

• 913000-16-5 (2,4-bis-benzyloxy-5-trifluoromethyl-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone 
• 1020065-79-5 (2,4-bis-benzyloxy-5-ethylphenyl)-(1,3-dihydroisoindol-2-yl)methanone 
• 1609699-97-9 (2,4-bis(benzyloxy)-5-(1H-pyrrolo[3,2-b]pyridin-1-yl)phenyl)(isoindolin-2-yl)methanone 
• 1609699-84-4 (2,4-dihydroxy-5-(phenylamino)phenyl)(isoindolin-2-yl)methanone 
• 1609699-85-5 (2,4-dihydroxy-5-(p-tolylamino)phenyl)(isoindolin-2-yl)methanone 
• 1609699-86-6 (5-((2,4-dichlorophenyl)amino)-2,4-dihydroxyphenyl)(isoindolin-2-yl)methanone 
• 1609699-69-5 1-(2,4-bis(benzyloxy)-5-(isoindoline-2-carbonyl)phenyl)-N-methyl-1H-indole-4-carboxamide 
• 1609699-95-7 1-(2,4-bis(benzyloxy)-5-(isoindoline-2-carbonyl)phenyl)-1H-indole-4-carboxylic acid 
• 1609699-63-9 N-(2-(1-(2,4-bis(benzyloxy)-5-(isoindoline-2-carbonyl)phenyl)-5-methoxy-1H-indol-3-yl)ethyl)acetamide 
• 1609699-64-0 (5-(3-(2-aminoethyl)-5-methoxy-1H-indol-1-yl)-2,4-bis(benzyloxy)phenyl)(isoindolin-2-yl)methanone 
• 1609699-65-1 methyl 2-(1-(2,4-bis(benzyloxy)-5-(isoindoline-2-carbonyl)phenyl)-1H-indol-3-yl)acetate 
• 1609699-66-2 (2,4-bis(benzyloxy)-5-(4-bromo-1H-indol-1-yl)phenyl)(isoindolin-2-yl)methanone 
• 1609699-67-3 (2,4-bis(benzyloxy)-5-(4-nitro-1H-indol-1-yl)phenyl)(isoindolin-2-yl)methanone 
• 1609699-68-4 methyl 1-(2,4-bis(benzyloxy)-5-(isoindoline-2-carbonyl)phenyl)-1H-indole-4-carboxylate 

Relevant articles and documents

Identification of a new series of potent diphenol HSP90 inhibitors by fragment merging and structure-based optimization

Heat shock protein 90 (HSP90) is a molecular chaperone to fold and maintain the proper conformation of many signaling proteins, especially some oncogenic proteins and mutated unstable proteins. Inhibition of HSP90 was recognized as an effective approach to simultaneously suppress several aberrant signaling pathways, and therefore it was considered as a novel target for cancer therapy. Here, by integrating several techniques including the fragment-based drug discovery method, fragment merging, computer aided inhibitor optimization, and structure-based drug design, we were able to identify a series of HSP90 inhibitors. Among them, inhibitors 13, 32, 36 and 40 can inhibit HSP90 with IC50 about 20-40 nM, which is at least 200-fold more potent than initial fragments in the protein binding assay. These new HSP90 inhibitors not only explore interactions with an under-studied subpocket, also offer new chemotypes for the development of novel HSP90 inhibitors as anticancer drugs.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound for use in medicine, the compound being a compound of the formula (VI0) or a salt, solvate, tautomer or N-oxide thereof: wherein the bicyclic group: is selected from the structures C1, C5 and C6: wherein n is 0, 1, 2 or 3; R1 is hydrogen, hydroxy, or O—Rz; R2a is hydroxy, methoxy or O—Rz; provided that at least one of R1 and R2a is O—Rz; Rz is Lp-Rp1; SO3H; a glucuronide residue; a mono-, di- or tripeptide residue; or Lp is a bond, C═O, (C═O)O, (C═O)NRp1 or S(O)xNRp1; x is 1 or 2; Rp1 is hydrogen or a an optionally substituted C1-25 hydrocarbyl group containing 0, 1 or 2 carbocyclic rings and 0, 1, 2, 3, 4, 5 or 6 carbon-carbon multiple bonds, provided that Rp1 is not hydrogen when Lp is a bond, C═O or (C═O)O; and provided also that O—Rz does not contain an O—O moiety; and excluding compounds wherein R1 is hydroxy and R2a is methoxy; Rp2 and Rp3 are the same or different and each is a group Rp1; and R3, R4a, R8 and R10 are defined in the claims. The compounds of formula (VI0) are pro-drugs of parent compounds wherein R1 and/or R2a are hydroxy, wherein the parent compounds have Hsp90 inhibiting activity.

PHARMACEUTICAL COMBINATIONS

The invention provides combinations comprising (or consisting essentially of) one or more ancillary compound(s) and a compound of the formula (I): or salts, tautomers, solvates and N-oxides thereof; wherein R1 is hydroxy or hydrogen; R2 is hydroxy; methoxy or hydrogen; provided that at least one of R1 and R2 is hydroxy; R3 is selected from hydrogen; halogen; cyano; optionally substituted C1-5 hydrocarbyl and optionally substituted C1-5 hydrocarbyloxy; R4 is selected from hydrogen; a group -(O)n-R7 where n is 0 or 1 and R7 is an optionally substituted acyclic C1-5 hydrocarbyl group or a monocyclic carbocyclic or heterocyclic group having 3 to 7 ring members; halogen; cyano; hydroxy; amino; and optionally substituted mono- or di-C1-5 hydrocarbyl-amino; or R3 and R4 together form a monocyclic carbocyclic or heterocyclic ring of 5 to 7 ring members; and NR5R6 forms an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 ring members are heteroatoms selected from oxygen, nitrogen and sulphur. The combinations have activity as Hsp90 and/or glycogen synthase kinase-3 and/or cyclin dependent kinase inhibitors.