496868-80-5

Basic information

• Product Name: 3-(AdaMantan-1-yl)-4'-broMobiphenyl-4-ol
• Synonyms: 3-(AdaMantan-1-yl)-4'-broMobiphenyl-4-ol
• CAS NO: 496868-80-5
• Molecular Formula: C₂₂H₂₃BrO
• Molecular Weight: 383.32142
• Mol File: 496868-80-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(AdaMantan-1-yl)-4'-broMobiphenyl-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(AdaMantan-1-yl)-4'-broMobiphenyl-4-ol(496868-80-5)
• EPA Substance Registry System: 3-(AdaMantan-1-yl)-4'-broMobiphenyl-4-ol(496868-80-5)

Safety Data

• Hazardous Substances Data: 496868-80-5(Hazardous Substances Data)

Upstream product

• 768-95-6 1-adamanthanol 
• 29558-77-8 4-bromo-4'-hydroxybiphenyl 

Downstream Products

• 496858-32-3 methyl E-3-(3’-adamantan-1-yl-4’-hydroxybiphenyl-4-yl) acrylate 
• 942626-92-8 4’-bromo-4-hydroxy-5-(adamantan-1-yl)biphenyl-3-carbaldehyde 
• 862650-81-5 methyl 3-(3’-adamantan-1-yl-4-hydroxybiphenyl-4-yl) propionate 
• 496868-77-0 Adarotene 
• 1232884-73-9 (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester 
• 1232886-16-6 ST₅₆₃₂ 
• 1232886-20-2 (E)-3-[3'-adamantan-1-yl-4'-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyloxy)biphenyl-4-yl]acrylic acid methyl ester 
• 1232886-33-7 (E)-3-(3'-adamantan-1-yl-4'-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid 
• 1232886-37-1 (E)-3-(3'-adamantan-1-yl-4'-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester 
• 1370009-32-7 acetic acid 3-adamantan-1-yl-4'-((E)-2-carboxyvinyl)biphenyl-4-yl ester 
• 1232885-04-9 ST₅₅₈₉ hydrochloride 
• 1232886-30-4 C₃₇H₄₇NO₅ 
• 1232885-10-7 C₃₈H₅₀N₂O₄ 

Relevant articles and documents

PHENOL DERIVATIVES FOR USE AS ANTIMICROBIAL, ANTIBACTERIAL, BACTERICIDE

Phenol derivatives of general formula (I) and (II), wherein meanings of the substituents are indicated in the description, their pharmaceutically acceptable salts, together with the processes for their preparation, their use as antimicrobial, antibacterial, bactericide agents and the corresponding pharmaceutical compositions are disclosed.

Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids

Atypical retinoids, or retinoid-related molecules (RRMs), represent a class of proapoptotic agents with a promising potential in the treatment of neoplastic diseases. In the present work, the synthesis and structure-activity relationship of a series of 3′-adamantan-1-yl-biphenyl-4-yl-acrylic acids substituted in ring A were studied. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocitic leukemia cell line (NB4), and in an ovarian carcinoma cell system including IGROV-1, carrying a functional wild-type p53, and a cisplatin-resistant subline, IGROV-1/Pt-1. The presence of at least one oxygenated substituent in positions 4′ or 5′ appears determinant for the antiproliferative activity. With two substituents of this kind the activity increases, particularly in the case of alkylenedioxy compounds. The activation of DNA damage response as indicated by phosphorylation of H2AX histone, RPA-2 protein, and p53 at serine 15 by the most apoptotic compounds provides additional support to the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this group.

A novel atypical retinoid endowed with proapoptotic and antitumor activity

The novel atypical retinoid E-3-(4′-hydroxy-3′-adamantylbiphenyl-4-yl)acrylic acid (ST1926, 4) exhibited a potent antiproliferative activity on a large panel of human tumor cells. Despite almost complete loss of ability to activate RARs, the compound was an effective apoptosis inducer and surprisingly produced DNA damage, that likely contributes to the proapoptotic activity. Following oral administration, 4 was well tolerated and caused tumor growth inhibition in the ovarian carcinoma, A2780/DX, and in the human melanoma, MeWo, growing in nude mice, thus supporting the therapeutic interest of the novel agent.