CAS: 52665-69-7; Ionophore A23187

该化合物是一种聚醚离子体抗生素,主要来自细菌发酵,* 链球菌病理* 其特点是能够将钙离子迁移到生物膜中,这可以显著影响细胞过程.卡西米辛表现出对二价电离子,特别是钙的高度亲和性,并且也可以与其他金属离子(例如镁和)结合.这种离子体的动作机制涉及形成一个含钙离子的复合体,方便它们通过脂肪膜,从而导致细胞信号和软骨的改变.在研究和临床环境中,卡西米辛因其具有调节钙过程的能力,在各个领域,包括癌症治疗和免疫学方面的潜在应用,已经进行了研究.但是,由于其毒性和不良效应的可能性,其使用往往受到限制.

结构式图片

欧盟法规

ECHA物质ECHA物质C&L通报REACH预注册

上下游产品

CAS号58288-38-3 (-)-calcimycin ... | CAS号78024-03-0 1-(1-tert-butyl... | CAS号86214-09-7 (2R,3R,6S,8S,9R... | CAS号81550-83-6 methyl 3-hydrox... | CAS号100845-53-2 (2R,3R,6S,8S,9R... | CAS号80657-88-1 (2R,4R)-2-methy... | CAS号79558-78-4 (2S,4S)-2-methy...

合成工艺路线路线简述

  • 合成目标产物 A23187 主要起始原料 4-Benzoxazolecarboxylic Acid, 5-[methyl(Trifluoroacetyl)Amino]-2-[[3,9,11-Trimethyl-8-[1-Methyl-2-Oxo-2-(1H-Pyrrol-2-yl)Ethyl]-1,7-Dioxaspiro[5.5]Undec-2-Yl]Methyl]-, Methyl Ester, [6S-[6α(2S*,3S*),8β(R*),9β,11α]]- (9CI)
  • (文献来源)合成步骤主要原料 4-Benzoxazolecarboxylic Acid, 5-[methyl(Trifluoroacetyl)Amino]-2-[[3,9,11-Trimethyl-8-[1-Methyl-2-Oxo-2-(1H-Pyrrol-2-yl)Ethyl]-1,7-Dioxaspiro[5.5]Undec-2-Yl]Methyl]-, Methyl Ester, [6S-[6α(2S*,3S*),8β(R*),9β,11α]]- (9Ci)
📜顺式-3,5-二甲基环己酮置于1,3-丙二硫醇,盐酸,Bis(Cyclohexyl)Aminomagnesium Bromide,三氟化硼乙醚,Sodium Methylate,Sodium Hydride,Lithium Thiopropiolate,对甲苯磺酸,臭氧,Magnesium,溶剂黄146,间氯过氧苯甲酸,Pyridinium Chlorochromate,Copper(II) Oxide,Copper Dichloride,锌体系中,用 甲醇,六甲基磷酰三胺,乙醚,二氯甲烷,苯 作为反应溶剂,化学反应生成 离子载体
参考文献:聚醚抗生素(-)-A23187(钙霉素)的全合成
标题:聚醚抗生素(-)-A23187(钙霉素)的全合成
摘要:(-)-A23187(钙霉素)的总合成通过收敛方法完成.合成的关键步骤是在碱性条件下将β-羟基酮立体定向环化成螺酮.
DOI:10.1016/s0040-4039(00)95911-2

海关参考信息

专利信息


专利号:US-11548898-B2
优先权日:2017-07-06
标题 :Synthesis of halichondrins
发明人:KISHI YOSHITO; AI YANRAN; YE NING; WANG QIAOYI; YAHATA KENZO; ISO Kentaro; NAINI SANTHOSH REDDY; YAMASHITA SHUJI; LEE JIHOON; OHASHI ISAO; FUKUYAMA TAKASHI
权利人:HARVARD COLLEGE; EISAI R&D MAN CO LTD
摘要:The present invention provides methods for the synthesis of ketones involving a Ni/Zr-mediated coupling reaction. The Ni/Zr-mediated ketolization reactions can be used in the synthesis of halichondrins (e.g., halichondrin A, B, C; homohalichondrin A, B, C; norhalichondrin A, B, C), and analogs thereof. Therefore, the present invention also provides synthetic methods useful for the synthesis of halichondrins, and analogs thereof. Also provided herein are compounds (i.e., intermediates) useful in the synthesis of halichondrins, and analogs thereof. In particular, the present invention provides methods and compounds useful in the synthesis of compound of Formula (H3-A).

专利号:US-4814347-A
优先权日:1985-07-22
标 题:Anthelmintic spiroketals and method of use
发明人:NELSON STEPHEN J
权利人:UPJOHN CO
摘要:This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.

专利号:US-6177572-B1
优先权日:1997-08-20
标题 :Solid and liquid-phase synthesis of benzoxazoles and benzothiazoles and their use
发明人:WANG FENGJIANG
权利人:SEPRACOR INC
摘要:Methods for preparing benzoxazoles and benzothiazoles on solid supports. Substituted benzothiazoles and benzoxazoles, libraries of the compounds, and methods of using the compounds are also disclosed.

专利号:WO-2008058514-A1
优先权日:2006-11-14
标 题:Preparations comprising boswellic acids for inhibiting the synthesis of prostaglandin e2
发明人:WERZ OLIVER; SIEMONEIT ULF
权利人:UNIV EBERHARD KARLS; WERZ OLIVER; SIEMONEIT ULF
摘要:The present invention relates to the use of preparations with pentacyclic triterpenoic acids and structural derivatives thereof, in particular boswellic acids from Boswellia species (such as B. serrata, B. carterii, B. sacra), for inhibiting the inducible mitochondrial prostaglandin E2 synthase-1. In addition, the invention relates to the use of pentacyclic triterpenoic acids and derivatives thereof for producing a medicament for the treatment of PGE2-mediated diseases.

专利号:US-4686297-A
优先权日:1985-07-22
标 题 :Anthelmintic spiroketals useful for killing parasitic worms
发明人:NELSON STEPHEN J
权利人:UPJOHN CO
摘要:This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.

专利号:US-4680419-A
优先权日:1985-07-22
标题:Spiroketals and process for preparing same
发明人:NELSON STEPHEN J
权利人:UPJOHN CO
摘要:This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.

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主要参考文献


1: Wu Q, Gou L, Lin S, Liang J, Yin J, Zhou X, Bai L, An D, Deng Z, Wang Z. Characterization of the N-methyltransferase CalM involved in calcimycin biosynthesis by Streptomyces chartreusis NRRL 3882. Biochimie. 2013 Jul;95(7):1487-93. doi: 10.1016/j.biochi.2013.03.014. Epub 2013 Apr 11. doi: 10.1007/s00253-013-4882-1. Epub 2013 May 12. doi: 10.1091/mbc.E10-09-0739. Epub 2011 Jul 27.
4: Pohl P, Antonenko YN, Yaguzhinsky LS. Kinetic properties of cation/H(+)-exchange: calcimycin (A23187)-mediated Ca2+/2H(+)-exchange on the bilayer lipid membrane. Biochim Biophys Acta. 1990 Sep 7;1027(3):295-300. doi: 10.1128/AAC.01130-10. Epub 2010 Dec 20.
7: Zeng GQ, Rui YC. [Inhibitory effect of dauricine on platelet activating factor released from calcimycin-induced mouse peritoneal macrophages]. Zhongguo Yao Li Xue Bao. 1990 Jul;11(4):346-50. Chinese. doi: 10.1016/j.rbmo.2015.06.013. Epub 2015 Jul 3. doi: 10.1159/000443059. Epub 2016 Mar 4. doi: 10.1002/asia.201500728. Epub 2015 Aug 28. doi: 10.1016/j.bbrc.2016.09.145. Epub 2016 Sep 28. doi: 10.1080/09168451.2014.963503. Epub 2014 Sep 25. doi: 10.1016/j.bbamem.2016.08.011. Epub 2016 Aug 25. e1-5. doi: 10.1002/asia.201300623. Epub 2013 Jul 23.

合成参考文献


参考文献:10.1007/s10863-010-9268-9
摘要:Fernandes MP, Inada NM, Chiaratti MR, Araújo FFB, Meirelles FV, Correia MTS, Coelho LCBB, Alves MJM, Gadelha FR, Vercesi AE. Mechanism of Trypanosoma cruzi death induced by Cratylia mollis seed lectin. Journal of Bioenergetics and Biomembranes. 2010 Feb 13;42(1):69–78. doi: 10.1007/s10863-010-9268-9.
参考文献:10.1124/jpet.111.183020
摘要:Chi Y, Li K, Yan Q, Koizumi S, Shi L, Takahashi S, Zhu Y, Matsue H, Takeda M, Kitamura M, Yao J. Nonsteroidal Anti-Inflammatory Drug Flufenamic Acid Is a Potent Activator of AMP-Activated Protein Kinase. The Journal of Pharmacology and Experimental Therapeutics. 2011 Oct;339(1):257–66. doi: 10.1124/jpet.111.183020.
参考文献:10.1007/s10534-011-9476-8
摘要:Hider RC, Kong XL. Glutathione: a key component of the cytoplasmic labile iron pool. Biometals. 2011 Dec;24(6):1179–87. doi: 10.1007/s10534-011-9476-8.
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