496868-77-0

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid is used as a pharmaceutical compound for its potential antitumor activity. It has been found to exhibit antitumor effects against various types of cancer, including acute myeloid leukemia, primary effusion lymphoma, prostate cancer, and glioma. (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid may also be useful in treating acute lung injury by suppressing inflammation and reactive oxygen species (ROS) through the inactivation of TLR4/NF-κB and p38/ERK1/2 signaling pathways.
Used in Drug Delivery Systems:
In the field of drug delivery, (2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid can be employed as a component in the development of novel drug delivery systems. These systems aim to enhance the compound's delivery, bioavailability, and therapeutic outcomes by utilizing various organic and metallic nanoparticles as carriers. This approach can potentially improve the efficacy of the compound in treating cancer and other diseases.

InChI:InChI=1S/C25H26O3/c26-23-7-6-21(20-4-1-16(2-5-20)3-8-24(27)28)12-22(23)25-13-17-9-18(14-25)11-19(10-17)15-25/h1-8,12,17-19,26H,9-11,13-15H2,(H,27,28)/b8-3+/t17-,18+,19-,25-

Upstream product

• 768-95-6 1-adamanthanol 
• 29558-77-8 4-bromo-4'-hydroxybiphenyl 
• 1232884-73-9 (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester 
• 1232885-04-9 ST₅₅₈₉ hydrochloride 
• 1232886-30-4 C₃₇H₄₇NO₅ 
• 1232885-10-7 C₃₈H₅₀N₂O₄ 
• 1232886-41-7 ST₅₆₆₇ trifluoroacetate 
• 1370009-35-0 (E)-3-[3'-adamantan-1-yl-4'-(2-methylaminoethylcarbamoyloxy)biphenyl-4-yl]acrylic acid hydrochloride 
• 1370009-41-8 C₃₈H₅₀N₂O₆ 
• 1232885-35-6 ST₅₆₀₆ hydrochloride 
• 496868-80-5 4-(4'-bromophenyl)-2-(adamantan-1-yl)phenol 
• 496858-32-3 methyl E-3-(3’-adamantan-1-yl-4’-hydroxybiphenyl-4-yl) acrylate 

Downstream Products

• 1232886-67-7 (E)-methanesulfonic acid 3-adamantan-1-yl-4'-(2-carboxyvinyl)-biphenyl-4-yl ester 
• 1232886-08-6 (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid tert-butyldiphenylsilyl ester 
• 1232885-64-1 ST₅₅₃₆ 
• 1232886-12-2 cyclopropanecarboxylic acid (E)-3-adamantan-1-yl-4'-(2-tert-butyldiphenylsilyloxycarbonylvinyl)biphenyl-4-yl ester 

Relevant academic research and scientific papers

Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors

To investigate the influence of the adamantyl group on the biological properties of known HDAC inhibitors with a 4-phenylcinnamic skeleton, a series of compounds having the adamantyl moiety in the cap structure were synthesized and compared to the corresponding hydroxamic acids lacking this group. An unexpected finding was the substantial reduction of inhibitory activity toward the tested enzymes, in particular HDAC6, following the introduction of the adamantyl group. In spite of the reduced ability to function as HDAC inhibitors, the compounds containing the adamantyl moiety still retained a good efficacy as antiproliferative and proapoptotic agents. A selected compound (2c; ST3056) of this series exhibited an appreciable antitumor activity against the colon carcinoma xenograft HCT116.

New retinoid derivatives as back-ups of Adarotene

Adarotene belongs to the so-called class of atypical retinoids. The presence of the phenolic hydroxyl group on Adarotene structure allows a rapid O-glucuronidation as a major mechanism of elimination of the drug, favoring a fast excretion of its glucuronide metabolite in the urines. A series of ether, carbamate and ester derivatives was synthesized. All of them were studied and evaluated for their stability at different pH. The cytotoxic activity in vitro on NCI-H460 non-small cell lung carcinoma and A2780 ovarian tumor cell lines was also tested. A potential back-up of Adarotene has been selected to be evaluated in tumor models.

Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity

Atypical retinoids (AR) represent a class of proapoptotic agents with promising potential in the treatment of neoplastic diseases. In the present work 4′-hydroxybiphenyl-4-ylacrylic acids were studied as a novel series of AR. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocytic 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 a bulky lipophilic group at position 3′ (adamantan-1-yl being the best) and the E configuration of the acrylic moiety appear essential for activity below 1 μM. No substitution on the rings or on the double bond improved the activity. A qualitative correlation between the log P and molecular volume of the 3′-substituent and the antiproliferative activity was found. From the study of a few selected compounds, it appears that the presence of the carboxylic group is an essential requirement for apoptogenic properties but not for antiproliferative activity, this being maintained in amide derivatives. On the other hand, compounds able to induce apoptosis produced a detectable level of genotoxic damage. This observation supports the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this class. Among the compounds investigated, E-3-(3′-adamantan-1-yl-4′- hydroxybiphenyl-4-yl)acrylic acid (2) was chosen for further investigation.

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.