[(1S,3S,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-11-methoxy-13-(2-methoxy-2-oxoethylidene)-21-[(4-methoxyphenyl)methoxy]-10,10-dimethyl-5-methylidene-12-octanoyloxy-19-oxo-17-[(1R)-1-(phenylmethoxymethoxy)ethyl]-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-25-yl] 2,4,6-trichlorobenzoate | 1159611-67-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: [(1S,3S,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-11-methoxy-13-(2-methoxy-2-oxoethylidene)-21-[(4-methoxyphenyl)methoxy]-10,10-dimethyl-5-methylidene-12-octanoyloxy-19-oxo-17-[(1R)-1-(phenylmethoxymethoxy)ethyl]-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-25-yl] 2,4,6-trichlorobenzoate
• CAS: 1159611-67-2
• 化学式: C₆₅H₈₃Cl₃O₁₆
• 分子量: 1226.72
• InChiKey: FOOBRVNCCCQUFE-JIBAKVBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  84
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(1S,3S,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-11-methoxy-13-(2-methoxy-2-oxoethylidene)-21-[(4-methoxyphenyl)methoxy]-10,10-dimethyl-5-methylidene-12-octanoyloxy-19-oxo-17-[(1R)-1-(phenylmethoxymethoxy)ethyl]-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-25-yl] 2,4,6-trichlorobenzoate 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium tetrafluoroborate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 13.5h， 以63%的产率得到[(1S,3S,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-11,21-dihydroxy-17-[(1R)-1-hydroxyethyl]-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-5-methylidene-12-octanoyloxy-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-25-yl] 2,4,6-trichlorobenzoate
  参考文献：
  名称：

  The Bryostatin 1 A-Ring Acetate is Not the Critical Determinant for Antagonism of Phorbol Ester-Induced Biological Responses

  摘要：

  The contribution of the A-ring C(7) acetate to the function of bryostatin 1 has been investigated through synthesis and biological evaluation of an analogue incorporating this feature into the bryopyran core structure. No enhanced binding affinity for protein kinase C (PKC) was observed, relative to previously characterized analogues lacking the C(7) acetate. Functional assays showed biological responses characteristic of those induced by the phorbol ester PMA and distinctly different from those observed with bryostatin 1.

  DOI：

  10.1021/ol900585t
• 作为产物：
  描述：

  (2S,3S,6S,E)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-hydroxy-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-4-(2-methoxy-2-oxoethylidene)tetrahydro-2H-pyran-3-yl octanoate 在 sodium chlorite 、 potassium dihydrogenphosphate 、 pyridine hydrofluoride 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 69.25h， 生成 [(1S,3S,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-11-methoxy-13-(2-methoxy-2-oxoethylidene)-21-[(4-methoxyphenyl)methoxy]-10,10-dimethyl-5-methylidene-12-octanoyloxy-19-oxo-17-[(1R)-1-(phenylmethoxymethoxy)ethyl]-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-25-yl] 2,4,6-trichlorobenzoate
  参考文献：
  名称：

  [EN] BRYOSTATIN ANALOGS AND USE THEREOF AS ANTIVIRAL AGENTS
  [FR] ANALOGUES DE LA BRYOSTATINE ET UTILISATION DE CEUX-CI EN TANT QU'AGENTS ANTIVIRAUX

  摘要：

  本文描述了三环大环内酯。这些大环内酯对蛋白激酶C（PKC）具有很高的结合亲和力。本文描述的化合物可用于多种治疗应用，包括治疗或预防病毒感染。本文还描述了生产大环内酯的方法。这些方法允许在较少的步骤中高产量地合成大环内酯，并具有高度的取代和特异性。

  公开号：

  WO2016025363A1

文献信息

• BRYOSTATIN ANALOGS AND USE THEREOF AS ANTIVIRAL AGENTS
  申请人：UNIVERSITY OF UTAH RESEARCH FOUNDATION

  公开号：US20170239212A1

  公开（公告）日：2017-08-24

  Described herein are tricyclic macrolactones. The macrolactones have a high binding affinity for PKC. The compounds described herein can be used in a number of therapeutic applications including the treatment or prevention of viral infection. Also described herein are methods for producing macrolactones. The methods permit the high-yield synthesis of macrolactones in a low number of steps and with a high degree of substitution and specificity.
• US9096550B2
  申请人：——

  公开号：US9096550B2

  公开（公告）日：2015-08-04
• The Bryostatin 1 A-Ring Acetate is Not the Critical Determinant for Antagonism of Phorbol Ester-Induced Biological Responses
  作者：Gary E. Keck、Wei Li、Matthew B. Kraft、Noemi Kedei、Nancy E. Lewin、Peter M. Blumberg

  DOI：10.1021/ol900585t

  日期：2009.6.4

  The contribution of the A-ring C(7) acetate to the function of bryostatin 1 has been investigated through synthesis and biological evaluation of an analogue incorporating this feature into the bryopyran core structure. No enhanced binding affinity for protein kinase C (PKC) was observed, relative to previously characterized analogues lacking the C(7) acetate. Functional assays showed biological responses characteristic of those induced by the phorbol ester PMA and distinctly different from those observed with bryostatin 1.
• [EN] BRYOSTATIN ANALOGS AND USE THEREOF AS ANTIVIRAL AGENTS<br/>[FR] ANALOGUES DE LA BRYOSTATINE ET UTILISATION DE CEUX-CI EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UNIV UTAH RES FOUND

  公开号：WO2016025363A1

  公开（公告）日：2016-02-18

  Described herein are tricyclic macrolactones. The macrolactones have a high binding affinity for PKC. The compounds described herein can be used in a number of therapeutic applications including the treatment or prevention of viral infection. Also described herein are methods for producing macrolactones. The methods permit the high-yield synthesis of macrolactones in a low number of steps and with a high degree of substitution and specificity.

  本文描述了三环大环内酯。这些大环内酯对蛋白激酶C（PKC）具有很高的结合亲和力。本文描述的化合物可用于多种治疗应用，包括治疗或预防病毒感染。本文还描述了生产大环内酯的方法。这些方法允许在较少的步骤中高产量地合成大环内酯，并具有高度的取代和特异性。