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152044-53-6

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  • 4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione,7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-,(1S,3S,7S,10R,11S,12S,16R)-

    Cas No: 152044-53-6

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152044-53-6 Usage

Uses

Different sources of media describe the Uses of 152044-53-6 differently. You can refer to the following data:
1. The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell.
2. Epothilone A is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Epothilone A acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity. Epothilone A has been investigated in clinical trials as an antitumour agent.

Definition

ChEBI: An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer).

Biological Activity

epothilone a (epo a) is a naturally occurring microtubule-stabilizing macrolide that was first isolated from the myxobacterium sorangium cellulosum. the ic50 value of epothilone a in hct-116 cell line is 4.4 nm [1].it has been found that the skov-3 human ovarian cancer cells were susceptible to epothilone a with ic50 value of 20.4 ± 1.4 nm [2]. the antiproliferative capacity of epothilone a in skov-3 cell line (measured as ic50 after 72 h continuous treatment) was six times greater than that of ptx’s. besides, epothilone a induced time coursedependent apoptosis and necrosis [2].

references

[1] regueiro-ren a1, borzilleri rm, zheng x, kim sh, johnson ja, fairchild cr, lee fy, long bh, vite gd. synthesis and biological activity of novel epothilone aziridines. org lett. 2001 aug 23;3(17):2693-6.[2] rogalska a1, marczak a, gajek a, szwed m, ?liwińska a, drzewoski j, jó?wiak z. induction of apoptosis in human ovarian cancer cells by new anticancer compounds, epothilone a and b. toxicol in vitro. 2013 feb;27(1):239-49.

Check Digit Verification of cas no

The CAS Registry Mumber 152044-53-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,2,0,4 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 152044-53:
(8*1)+(7*5)+(6*2)+(5*0)+(4*4)+(3*4)+(2*5)+(1*3)=96
96 % 10 = 6
So 152044-53-6 is a valid CAS Registry Number.
InChI:InChI=1/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1

152044-53-6Upstream product

152044-53-6Relevant articles and documents

Total synthesis of epothilone A.

Zhu,Panek

, p. 2575 - 2578 (2000)

[reaction: see text]Epothilones A (1) and B (2) are potent antitumor natural products with a Taxol-like mechanism of action. A total synthesis of epothilone A (1) is reported, which utilized chiral silane-based bond construction methodology to introduce t

Epothilones C, E and F

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Page 8, (2008/06/13)

Epothilone derivatives are obtained by: (1) cultivation of Sorangium cellulosum DSM 6773 in the presence of an absorption resin; (2) separation of the resin and culture followed by washing with aqueous methanol; (3) eluting the washed resin with methanol and reducing the extract; (4) partitioning the extract between methanol and hexane; (5) reducing the methanolic phase and fractionating it on a Sephadex column, and (6) isolation of the epothilones by chromatography using a methanol/water mixture. Epothilone A is followed by epothilone B, and two further fractions.

Epothilone derivatives, their preparation and utilization

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Page 15-16, (2008/06/13)

Epothilone derivatives of formula (I)-(III) are new. R = H or 1-4C alkyl; Y Z = H, halo, pseudohalogen, OH, 1-6C acyloxy, 1-6C alkoxy or benzoyloxy; or Y+Z = bond or O; (a) R' = Q; A = H; B = OR1; and R" = R2; or R"+B = C(O)O, C(S)O, S(O)O, Si(R")2O or C(

Aldolase-catalyzed asymmetric synthesis of novel pyranose synthons as a new entry to heterocycles and epothilones

Liu, Junjie,Wong, Chi-Huey

, p. 1404 - 1407 (2007/10/03)

Enzymatic reactions catalyzed by DERA provide the basis for a new strategy for the synthesis of novel pyranose synthons. The utility of this very convergent and effective method is demonstrated by the concise total synthesis of epothilones (see scheme; DERA = 2-deoxyribose-5-phosphate aldolase).

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