1072121-88-0

Basic information

• Product Name: C₁₈H₁₇NO₄
• Synonyms: C₁₈H₁₇NO₄
• CAS NO: 1072121-88-0
• Molecular Weight: 311.337
• Mol File: 1072121-88-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₈H₁₇NO₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₈H₁₇NO₄(1072121-88-0)
• EPA Substance Registry System: C₁₈H₁₇NO₄(1072121-88-0)

Safety Data

• Hazardous Substances Data: 1072121-88-0(Hazardous Substances Data)

Upstream product

• 1133778-31-0 cis-3,4',5-trimethoxy-3'-aminostilbene hydrochloride 
• 503-38-8 trichloromethyl chloroformate 
• 586410-12-0 (Z)-5-(3,5-dimethoxystyryl)-2-methoxyaniline 

Downstream Products

• 1072121-47-1 (Z)-{5-[2-(3,5-dimethoxyphenyl)-ethenyl]-2-methoxy-phenyl}carbamic acid 2-morpholin-4-yl-ethyl ester 
• 1072121-45-9 (Z)-{5-[2-(3,5-dimethoxyphenyl)-ethenyl]-2-methoxyphenyl}carbamic acid 2-[2-(2-hydroxyethoxy)ethoxy]ethyl ester 
• 1072121-46-0 (Z)-1-{5-[2-(3,5-dimethoxyphenyl)-ethenyl]-2-methoxyphenyl}-3-(2-morpholin-4-yl-ethyl)-urea 
• 1072121-74-4 {5-[2-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl}-urea 
• 1072121-78-8 (Z) 1-{5-[2-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl}-3-(2-morpholin-4-yl-ethyl)-urea hydrochloride 
• 1072121-73-3 (Z)-{5-[2-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenyl}-carbamic acid 2-morpholin-4-yl-ethyl ester oxalate 

Relevant articles and documents

A novel hybrid drug between two potent anti-tubulin agents as a potential prolonged anticancer approach

We report the design, synthesis and biological characterisation of a novel hybrid drug by conjugation of two tubulin inhibitors, a hemiasterlin derivative A (H-Mpa-Tle-AHA-OH), obtained by condensation of three non-natural amino acids, and cis-3,4′,5-trimethoxy-3′aminostilbene (B). As we have previously demonstrated synergy between A and B, we used a monocarbonyl derivative of triethylene glycol as linker (L) to synthesise compounds A-L and A-L-B; via HPLC we analysed the release of its potential hydrolysis products A, A-L, B and B-L in physiological fluids: the hybrid A-L-B undergo hydrolysis in rat whole blood of the ester bond between A and L (half-life = 118.2 ± 9.5 min) but not the carbamate bond between B and L; the hydrolysis product B-L was further hydrolyzed, but with a slower rate (half-life = 288 ± 12 min). The compound A-L was the faster hydrolyzed conjugate (half-life = 25.4 ± 1.1 min). The inhibitory activity of the compounds against SKOV3 ovarian cancer cell growth was analysed. The IC50 values were 7.48 ± 1.27 nM for A, 40.3 ± 6.28 nM for B, 738 ± 38.5 nM for A-L and 37.9 ± 2.11 nM for A-L-B. The anticancer effect of A-L-B was evidenced to be obtained via microtubule dynamics suppression. Finally, we stated the expression of the active efflux transporters P-gp (ABCB1) and MRP1 (ABCC1) in the human normal colon epithelial NCM460 cell line by reverse-transcription PCR. Via permeation studies across NCM460 monolayers we demonstrate the poor aptitude of A to interact with active efflux transporters (AET): indeed, the ratio between its permeability coefficients for the basolateral (B) → apical (A) and B → A transport was 1.5 ± 0.1, near to the ratio of taltobulin (1.12 ± 0.06), an hemiasterlin derivative able to elude AETs, and significantly different form the ratio of celiprolol (3.4 ± 0.2), an AET substrate.

STILBENE DERIVATIVES AS NEW CANCER THERAPEUTIC AGENTS

Stilbene derivatives exhibit killing and suppression of growth activity against a variety of cancer cells, and are effective at suppressing tumor growth in vivo. The stilbene derivatives may be used in the treatment of diseases characterized by cell hyperproliferation including human malignancies and non-malignant diseases such as liver cirrhosis. Stilbenes may also disrupt abnormal vessels in tumor to achieve vascular disrupting effect to suppress tumor growth. Water soluble pro-drug forms of stilbene derivatives are particularly useful in suppressing tumor growth in vivo.