172931-93-0

Basic information

• Product Name: CHEMBRDG-BB 6523984
• Synonyms: CHEMBRDG-BB 6523984;4-(2-NAPHTHYLMETHOXY)BENZALDEHYDE;4-(2-naphthylmethoxy)benzaldehyde(SALTDATA: FREE)
• CAS NO: 172931-93-0
• Molecular Formula: C₁₈H₁₄O₂
• Molecular Weight: 262.3
• Mol File: 172931-93-0.mol

Chemical Properties

• Boiling Point: 459.6°C at 760 mmHg
• Flash Point: 214.5°C
• Appearance: /
• Density: 1.192g/cm³
• Vapor Pressure: 1.25E-08mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: CHEMBRDG-BB 6523984(CAS DataBase Reference)
• NIST Chemistry Reference: CHEMBRDG-BB 6523984(172931-93-0)
• EPA Substance Registry System: CHEMBRDG-BB 6523984(172931-93-0)

Safety Data

• Hazardous Substances Data: 172931-93-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H14O2/c19-12-14-6-9-18(10-7-14)20-13-15-5-8-16-3-1-2-4-17(16)11-15/h1-12H,13H2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 2506-41-4 1-chloromethylnaphthalene 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 131340-67-5 3-(naphth-2-ylmethoxy)benzaldehyde 

Relevant articles and documents

Development of hydroxy-based sphingosine kinase inhibitors and anti-inflammation in dextran sodium sulfate induced colitis in mice

Sphingosine kinase (SphK)-catalyzed production of sphingosine-1-phosphate (S1P) regulates cell growth, survival and proliferation as well as inflammatory status in animals. In recent study we reported the N′-(3-(benzyloxy)benzylidene)-3,4,5-trihydroxybenzohydrazide scaffold as a potent SphK inhibitor. As a continuation of these efforts, 51 derivatives were synthesized and evaluated by SphK1/2 inhibitory activities for structure-activity relationship (SAR) study. Among them, 33 was identified as the most potent SphK inhibitor. Potency of 33 was also observed to efficiently decrease SphK1/2 expression in human colorectal cancer cells (HCT116) and significantly inhibit dextran sodium sulfate (DSS)-induced colitis as well as the decreased expression of interleukin (IL)-6 and cyclooxygenase-2 (COX-2) in mouse models. Collectively, 33 was validated as an effective SphK inhibitor, which can be served as anti-inflammatory agent to probably treat inflammatory bowel diseases in human.

Chalcone derivatives and drugs containing the same

PCT No. PCT/JP97/01652 Sec. 371 Date Nov. 17, 1998 Sec. 102(e) Date Nov. 17, 1998 PCT Filed May 16, 1997 PCT Pub. No. WO97/44306 PCT Pub. Date Nov. 27, 1997This invention relates to chalcone derivatives represented by the following formula (1): wherein A represents a phenyl group, a quinolyl group or the like, W represents a vinylene group or the like, and R1 to R5 each independently represent a carboxyl, cyano, alkyloxycarbonyl or like group, or salts of the chalcone derivatives, and also to drugs containing them as effective ingredients. These compounds have excellent cys-LT receptor antagonism, and are useful as antiallergic agents or the like.

BENZYLIDENE RHODANINES

This invention provides novel benzylidene rhodanines which are useful as agents in treating or preventing conditions associated with . beta.-amyloid peptide. This invention further provides methods of treating or preventing Alzheimer's Disease which comprises administering to a mammal in need thereof an effective amount of one or more of the benzylidene rhodanines of the present invention.

Synthesis and structure-activity relationships of carboxylated chalcones: A novel series of CysLT1 (LTD4) receptor antagonists

The synthesis and CysLT1 antagonistic activities of a new series of 2- , 3-, and 4-(2-quinolinylmethoxy)- and 3- and 4-[2-(2-quinolinyl)ethenyl]- substituted, 2'-, 3'-, 4'-, or 5'-carboxylated chalcones are described. Structure-activity relationship studies indicate a preference for the presence of a negatively charged (acidic) moiety, although in some cases nitrile or ester analogues also exhibit moderate activity. The quinoline moiety may be substituted at either the 3- or the 4-position. Replacement of this heterocycle by other aromatic groups results in compounds with comparable affinities [2-(7-chloroquinoline), 1-(1-methyl-2-benzimidazole), or 1-(2-benzothiazole)] or substantially lower activities [1-(1- ethoxyethyl)-2-benzimidazole, 2-naphthyl, or phenyl]. The quinoline and chalcone moieties may be connected by either an ethenyl or a methoxy spacer. The acidic moiety at the chalcone B ring may be attached to the 2'-, 3'-, 4'- , or 5'-position, for both the 3- and 4-substituted chalcones. There are no general patterns to specify which substitution positions gave the most potent compounds. The series contains several potent CysLT1 receptor antagonists, with K(D) values approaching the nanomolar range, as measured by the displacement of [3H]LTD4 from guinea pig lung membranes. Antagonism of LTD4-induced contraction of guinea pig ileum, the inhibition of antigen- induced contraction of guinea pig trachea in vitro, and the inhibition of LTD4-induced increase of vascular permeability in vivo are determined for chalcones with high CysLT1 receptor affinities (K(D) values below 0.1μM). 2'-Hydroxy-4-(2-quinolinylmethoxy)-5'-(5-tetrazolyl)chalcone (14, VUF 4819) showed good activity in both in vitro and in vivo assays and has been selected for further evaluation.