244126-41-8

Usage

Type of Compound

Synthetic derivative of sphingosine

Natural Occurrence

Sphingosine is a natural lipid found in cell membranes

Therapeutic Applications

Potential anti-cancer and pro-apoptotic properties

Enzyme Inhibition

Inhibits protein kinase C (PKC) and ceramide glucosyltransferase (CGT)

Role of Enzymes

PKC and CGT play a role in cell growth and survival

Preclinical Studies

Shown promise in inhibiting PKC and CGT

Combination Therapy

Being investigated for use in combination with chemotherapeutic agents to enhance effectiveness in cancer treatment

Further Research

Needed to understand full therapeutic potential and any potential side effects

Upstream product

• 111726-43-3 3,4-(methylenedioxy)phenyl methoxymethyl ether 
• 120046-45-9 5-(methoxymethoxy)benzo[d][1,3]-dioxole-4-carbaldehyde 
• 533-31-3 Sesamol 
• 107-30-2 chloromethyl methyl ether 
• 316800-43-8 formic acid 5-methoxymethoxy-benzo[1,3]dioxol-4-yl ester 

Downstream Products

• 23780-63-4 4,5-Dihydroxy-1,3-benzdioxol 
• 360778-72-9 (3R,5R)-3-(7-Hydroxy-6-methoxymethoxy-benzo[1,3]dioxol-4-yl)-6,6-dimethyl-5-phenyl-morpholin-2-one 
• 874758-53-9 hydroxy-(7-hydroxy-6-methoxymethoxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester 
• 874758-54-0 hydroxy-(6-methoxymethoxy-7-trifluoromethanesulfonyloxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester 
• 874758-69-7 C₆₀H₆₁Cl₃N₄O₁₅S 
• 114899-77-3 ecteinascidin 743 
• 114899-80-8 (1'R,6R,6aR,7R,13S,14R,16R)-5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8-dihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinoline]-14-carbonitrile 
• 442663-24-3 2-(tert-butyl-diphenyl-silanyloxy)-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethylamine 
• 442663-41-4 Trifluoro-methanesulfonic acid 7-((3R,5R)-6,6-dimethyl-2-oxo-5-phenyl-morpholin-3-yl)-5-methoxymethoxy-benzo[1,3]dioxol-4-yl ester 
• 442663-42-5 Trifluoro-methanesulfonic acid 7-[(R)-2-hydroxy-1-((R)-2-hydroxy-2-methyl-1-phenyl-propylamino)-ethyl]-5-methoxymethoxy-benzo[1,3]dioxol-4-yl ester 
• 442663-43-6 (R)-1-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethylamino]-2-methyl-1-phenyl-propan-2-ol 
• 442663-30-1 Acetic acid (R)-2-[(S)-3-(3-benzyloxy-2-iodo-4-methoxy-5-methyl-benzyl)-6-methyl-2,5-dioxo-piperazin-1-yl]-2-(6-hydroxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl ester 
• 442663-23-2 Trifluoro-methanesulfonic acid 7-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2-hydroxy-2-methyl-1-phenyl-propylamino)-ethyl]-5-methoxymethoxy-benzo[1,3]dioxol-4-yl ester 
• 442663-49-2 mecyl body 

Relevant academic research and scientific papers

Design, synthesis and characterization of potent microtubule inhibitors with dual anti-proliferative and anti-angiogenic activities

Microtubule has been an important target for anticancer drug development. Here we report the discovery and characterization of a series of fused 4-aryl-4H-chromene-based derivatives as highly potent microtubule inhibitors. Among a total of 37 derivatives synthesized, 23 exhibited strong in vitro anti-proliferative activities against A375 human melanoma cells. The relationship between the biological activities of these microtubule inhibitors and their chemical structure variations was analyzed. Studies of compounds 27a, 19a and 9a in parallel with colchicine as the positive control compound in a panel of biological assays revealed that these compounds blocked cell cycle progression, increased apoptosis, and inhibited HUVEC capillary tube formation at low nanomolar concentrations. The most potent compound 27a was also tested in eight additional cancer cell lines besides A375 cells and two non-cancer cells and showed potent and selective activity on these cancer cells. To understand the molecular and structure mechanism of action of these compounds, tubulin polymerization and molecular docking studies were carried out for 27a as the representative. The results were consistent with the mechanism by which 27a interacts with the colchicine binding site on tubulin and disrupts tubulin polymerization. With potent dual actions of microtubule destabilization and vascular disruption described above, this small molecule can serve as a valuable research probe of the function and role of microtubules in human diseases and promising lead for developing new therapeutic agents.

Intermediate and process of preparation of ecteinascidin using such intermediate

The present invention concerns an intermediate of the following formula I in which R1 and R2 represent independently of each other a C1-C12 alkyl group, a (C1-C12 alkoxy)carbonyl group, opt

Total synthesis of ecteinascidin 743

A convergent total synthesis of ecteinascidin 743 is realized from five building blocks of almost equal size. It takes 23 steps from l-3-hydroxy-4-methoxy-5-methyl phenylalanol (5) with an overall yield of 3%. Copyright

PROCESS FOR TOTAL SYNTHESIS OF ECTEINASCIDINS AND INTERMEDIATES THEREFOR

An intermediate compound for total synthesis of ecteinascidins comprising, a compound represented by general formula 2 having thioether group at C4 site, and the substituent R2 of N12 site is trichloroethoxicarbonyl (Troc) to which various substituents can be introduced by mild condition, further having 10 members ring structure which can be converted to a ring of other numbered members.

Total synthesis of ecteinascidin 743

The total synthesis of ecteinascidin 743 (1), an extremely potent antitumor agent, has been accomplished. The synthesis features Ugi's 4CC reaction, intramolecular Heck reaction, phenol-aldehyde cyclization, and acid-induced intramolecular sulfide formation. Copyright

New syntheses of dillapiol [4,5-dimethoxy-6-(2-propenyl)-1,3-benzodioxole], its 4-methylthio and other analogs

Three syntheses of the natural synergist dillapiol from the natural, commercially available sesamol as starting material, are described. A major difference between these is the order of introduction of the additional methoxy and allyl substituents. In one

Synthetic study on ecteinascidin 743 starting from D-glucose

During the course of synthetic study on ecteinascidin 743 (1), key intermediate 5 was prepared. Stereocontrolled synthesis of 5 from D-glucose was accomplished using incorporation of two nitrogen atoms and stereoselective addition of a phenol to an imine