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69866-21-3
  • names:

    4-Hydroxy-7-(4-hydroxy-5-methoxy-7-((7bR,8aS)-7-methyl-4-oxo-1,2,4,5,8,8a-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-2-carbonyl)-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-3-carbonyl)-5-methoxy-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxamide

  • CAS号:

    69866-21-3

    MDL Number:
  • MF(分子式): C37H33N7O8 MW(分子量): 703.71
  • EINECS: Reaxys Number:
  • Pubchem ID: Brand:BIOFOUNT
Rachelmycin
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中文别名 4-Hydroxy-7-(4-hydroxy-5-methoxy-7-((7bR,8aS)-7-methyl-4-oxo-1,2,4,5,8,8a-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-2-carbonyl)-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-3-carbonyl)-5-methoxy-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxamide
英文别名 CC1065; CC 1065; CC-1065; NSC298223; NSC 298223; NSC-298223; Rachelmycin
CAS号 69866-21-3
Inchi InChI=1S/C37H33N7O8/c1-14-12-39-27-22(45)10-23-37(24(14)27)11-15(37)13-44(23)35(49)21-9-18-16-4-6-42(28(16)30(46)32(51-2)25(18)41-21)34(48)20-8-19-17-5-7-43(36(38)50)29(17)31(47)33(52-3)26(19)40-20/h8-10,12,15,39-41,46-47H,4-7,11,13H2,1-3H3,(H2,38,50)/t15-,37+/m1/s1
InchiKey UOWVMDUEMSNCAV-WYENRQIDSA-N
分子式 Formula C37H33N7O8
分子量 Molecular Weight 703.71
溶解度Solubility
性状 Solid powder
储藏条件 Storage conditions Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).
产品说明 Rachelmycin(CAS:69866-21-3):仅限应用于工业或者科学研究过程中非医疗目的,不应用于人类或动物的临床诊断以及治过程疗,该产品非药用,非食用。
IntroductionRachelmycin is a novel and potent DNA-alkylating agent which inhibits TBP/DNA interaction.
Application1
Application2
Application3
警示图
危险性 Warning
危险性警示
安全声明
安全防护
备注
[1]Tietze LF, Krewer B, von Hof JM, Frauendorf H, Schuberth I. Determination of the biological activity and structure activity relationships of drugs based on the highly cytotoxic duocarmycins and CC-1065. Toxins (Basel). 2009 Dec;1(2):134-50. doi: 10.3390/toxins1020134. Epub 2009 Dec 2. PubMed PMID: 22069536; PubMed Central PMCID: PMC3202783.
[2]Chavda S, Babu B, Yanow SK, Jardim A, Spithill TW, Kiakos K, Kluza J, Hartley JA, Lee M. A novel achiral seco-cyclopropylpyrido[e]indolone (CPyI) analog of CC-1065 and the duocarmycins: synthesis, DNA interactions, in vivo anticancer and anti-parasitic evaluation. Bioorg Med Chem. 2010 Jul 15;18(14):5016-24. doi: 10.1016/j.bmc.2010.05.078. Epub 2010 Jun 4. PubMed PMID: 20579889.
[3] Wu S, Jian XH, Yuan H, Jin WB, Yin Y, Wang LY, Zhao J, Tang GL. Unified Biosynthetic Origin of the Benzodipyrrole Subunits in CC-1065. ACS Chem Biol. 2017 Jun 16;12(6):1603-1610. doi: 10.1021/acschembio.7b00302. Epub 2017 May 2. PubMed PMID: 28426198.
[4] Jin WB, Wu S, Jian XH, Yuan H, Tang GL. A radical S-adenosyl-L-methionine enzyme and a methyltransferase catalyze cyclopropane formation in natural product biosynthesis. Nat Commun. 2018 Jul 17;9(1):2771. doi: 10.1038/s41467-018-05217-1. PubMed PMID: 30018376; PubMed Central PMCID: PMC6050322.
[5] Yuan H, Zhang J, Cai Y, Wu S, Yang K, Chan HCS, Huang W, Jin WB, Li Y, Yin Y, Igarashi Y, Yuan S, Zhou J, Tang GL. GyrI-like proteins catalyze cyclopropanoid hydrolysis to confer cellular protection. Nat Commun. 2017 Nov 14;8(1):1485. doi: 10.1038/s41467-017-01508-1. PubMed PMID: 29133784; PubMed Central PMCID: PMC5684135.
6: Mullins EA, Shi R, Eichman BF. Toxicity and repair of DNA adducts produced by the natural product yatakemycin. Nat Chem Biol. 2017 Sep;13(9):1002-1008. doi: 10.1038/nchembio.2439. Epub 2017 Jul 24. PubMed PMID: 28759018; PubMed Central PMCID: PMC5657529.7: Chanda PB, Boyle KE, Brody DM, Shukla V, Boger DL. Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) alkylation subunit. Bioorg Med Chem. 2016 Oct 15;24(20):4779-4786. doi: 10.1016/j.bmc.2016.04.050. Epub 2016 Apr 26. PubMed PMID: 27221071; PubMed Central PMCID: PMC5052114.8: Uematsu M, Brody DM, Boger DL. A five-membered lactone prodrug of CBI-based analogs of the duocarmycins. Tetrahedron Lett. 2015 Jun 3;56(23):3101-3104. PubMed PMID: 26069351; PubMed Central PMCID: PMC4459655.9: Patil PC, Satam V, Lee M. A Short Review on the Synthetic Strategies of Duocarmycin Analogs that are Powerful DNA Alkylating Agents. Anticancer Agents Med Chem. 2015;15(5):616-30. Review. PubMed PMID: 25511515.10: Wolfe AL, Duncan KK, Parelkar NK, Weir SJ, Vielhauer GA, Boger DL. A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct. J Med Chem. 2012 Jun 28;55(12):5878-86. doi: 10.1021/jm300330b. Epub 2012 Jun 12. PubMed PMID: 22650244; PubMed Central PMCID: PMC3386426.1
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