{(2R,6R)-6-[(2S,4S)-2-(2-{(E)-3-[(2R,3R,4S,5R,6R)-4-Hydroxy-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-[1,3]dioxan-4-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde | 879872-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: {(2R,6R)-6-[(2S,4S)-2-(2-{(E)-3-[(2R,3R,4S,5R,6R)-4-Hydroxy-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-[1,3]dioxan-4-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde
• 英文别名: 2-[(2R,6R)-6-[[(2S,4S)-2-[2-[(E)-3-[(2R,3R,4S,5R,6R)-4-hydroxy-6-[(E)-1-iodoprop-1-en-2-yl]-3,5-dimethyloxan-2-yl]prop-1-enyl]-1,3-oxazol-4-yl]-1,3-dioxan-4-yl]methyl]-4-methylideneoxan-2-yl]acetaldehyde
• CAS: 879872-52-3
• 化学式: C₂₉H₄₀INO₇
• 分子量: 641.544
• InChiKey: HCRUTESVNKRBRH-PSAMCKMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {(2R,6R)-6-[(2S,4S)-2-(2-{(E)-3-[(2R,3R,4S,5R,6R)-4-Hydroxy-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-[1,3]dioxan-4-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde 在 18-冠醚-6 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.92h， 生成 (1S,6E,9R,11R,12R,13S,16Z,19S,23R,25S,31S)-11-[(E)-1-iodoprop-1-en-2-yl]-12,31-dimethyl-21-methylidene-4,10,14,28,29,30-hexaoxa-32-azapentacyclo[23.3.1.12,5.19,13.119,23]dotriaconta-2,5(32),6,16-tetraen-15-one
  参考文献：
  名称：

  Design and Synthesis of a Potent Phorboxazole C(11−15) Acetal Analogue

  摘要：

  We disclose here the design, synthesis, and biological evaluation of simplified Z- and E-C(2-3) alkynyl phorboxazole C(11-15) acetals (+)-7Z and (+)-7E, wherein the Z-isomer proved to be a potent nanomolar cytotoxic agent. Reevaluation of (+)-C(45-46) E-chloroalkenyl phorboxazole A (6) confirms subnanomolar activity across a broad panel of human cancer cell lines.

  DOI：

  10.1021/ol060014v
• 作为产物：
  描述：

  {(2R,6R)-6-[(2S,4S)-2-(2-{(E)-3-[(2R,3S,4S,5R,6R)-4-(2,4-Dimethoxy-benzyloxy)-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-[1,3]dioxan-4-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde 在 phosphate buffer 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到{(2R,6R)-6-[(2S,4S)-2-(2-{(E)-3-[(2R,3R,4S,5R,6R)-4-Hydroxy-6-((E)-2-iodo-1-methyl-vinyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-4-yl)-[1,3]dioxan-4-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-acetaldehyde
  参考文献：
  名称：

  Design and Synthesis of a Potent Phorboxazole C(11−15) Acetal Analogue

  摘要：

  We disclose here the design, synthesis, and biological evaluation of simplified Z- and E-C(2-3) alkynyl phorboxazole C(11-15) acetals (+)-7Z and (+)-7E, wherein the Z-isomer proved to be a potent nanomolar cytotoxic agent. Reevaluation of (+)-C(45-46) E-chloroalkenyl phorboxazole A (6) confirms subnanomolar activity across a broad panel of human cancer cell lines.

  DOI：

  10.1021/ol060014v

文献信息

• Phorboxazole compounds and methods of their preparation
  申请人：The Trustees of the University of Pennsylvania

  公开号：US07485631B2

  公开（公告）日：2009-02-03

  Novel macrolactone compounds, their methods of preparation, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the macrolactone compounds may be useful, inter alia, for treating various cancers, inducing apoptosis in malignant cells, or inhibiting cancer cell division.

  新型大环内酯化合物，其制备方法，含有这些化合物的药物组合物，以及这些药物的药用方法被披露。在某些实施例中，这些大环内酯化合物可能有助于治疗各种癌症，诱导恶性细胞凋亡，或抑制癌细胞分裂。
• [EN] HEMI-PHORBOXAZOLE A DERIVATIVES AND METHODS OF THEIR USE<br/>[FR] DÉRIVÉS DE L'HÉMI-PHORBOXAZOLE A ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV PENNSYLVANIA

  公开号：WO2011011665A1

  公开（公告）日：2011-01-27

  The present invention is directed to hemi phorboxazole A: and its stereoisomers, as well as derivatives of hemi phorboxazole A of formula I: wherein ring A is aryl or a 5- or 6-membered heteroaryl optionally substituted with one or more of halogen, -OH, or -C1-6alkyl; and R is-CN, a 5- or 6-membered heteroaryl, or halogen; and the pharmaceutically acceptable salt forms thereof, in addition to methods of using these compounds.

  本发明涉及半磷酸酯A及其立体异构体，以及公式I中的半磷酸酯A的衍生物：其中环A是芳基或5-或6-成员杂芳基，可以选择地被一个或多个卤素，-OH或-C1-6烷基取代；R是-CN，5-或6-成员杂芳基，或卤素；以及其药用盐形式，以及使用这些化合物的方法。
• Phorboxazole Compounds and Methods of Their Preparation
  申请人：Razler Thomas M.

  公开号：US20090163563A1

  公开（公告）日：2009-06-25

  Novel macrolactone compounds, their methods of preparation, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the macrolactone compounds may be useful, inter alia, for treating various cancers, inducing apoptosis in malignant cells, or inhibiting cancer cell division.
• HEMI-PHORBOXAZOLE A DERIVATIVES AND METHODS OF THEIR USE
  申请人：Smith, III Amos B.

  公开号：US20130030027A1

  公开（公告）日：2013-01-31

  The present invention is directed to hemi phorboxazole A: and its stereoisomers, as well as derivatives of hemi phorboxazole A of formula I: wherein ring A is aryl or a 5- or 6-membered heteroaryl optionally substituted with one or more of halogen, —OH, or —C 1-6 alkyl; and R is —CN, a 5- or 6-membered heteroaryl, or halogen; and the pharmaceutically acceptable salt forms thereof, in addition to methods of using these compounds.
• US7485631B2
  申请人：——

  公开号：US7485631B2

  公开（公告）日：2009-02-03