scabrosin acetate butyrate | 220345-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: scabrosin acetate butyrate
• 英文别名: Ambewelamide A；[(1R,4S,5R,7S,8S,12R,15S,16R,18S,19S)-19-acetyloxy-2,13-dioxo-6,17-dioxa-23,24-dithia-3,14-diazaoctacyclo[10.10.2.01,14.03,12.04,10.05,7.015,21.016,18]tetracosa-9,20-dien-8-yl] butanoate
• CAS: 220345-71-1
• 化学式: C₂₄H₂₄N₂O₈S₂
• 分子量: 532.595
• InChiKey: OBYDDBDJKUQGLS-BIQXIOCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 scabrosin acetate butyrate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 以37%的产率得到[(1R,4S,5R,7S,8S,12R,15S,16R,18S,19S)-19-acetyloxy-1,12-bis(acetylsulfanyl)-2,13-dioxo-6,17-dioxa-3,14-diazaheptacyclo[12.8.0.03,12.04,10.05,7.015,21.016,18]docosa-9,20-dien-8-yl] butanoate
  参考文献：
  名称：

  Scabrosin esters and derivatives: chemical derivatization studies and biological evaluation

  摘要：

  Several derivatives of the natural scabrosin esters were synthesized in order to elucidate the structural features present, which are responsible for the biological activities. The studies demonstrate that full anti-proliferative activities of the scabrosin esters, both the carboskeleton core as well as the ability to form the dithiol and/or the disulfide linkage of the epidithiopiperazine-2,5-dione are required. The presence of the epoxide rings on the scabrosin esters do not contribute to the observed biological activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.015

文献信息

• Scabrosin esters and derivatives: chemical derivatization studies and biological evaluation
  作者：Christina L.L. Chai、John A. Elix、Paul B. Huleatt、Paul Waring

  DOI：10.1016/j.bmc.2004.08.015

  日期：2004.11

  Several derivatives of the natural scabrosin esters were synthesized in order to elucidate the structural features present, which are responsible for the biological activities. The studies demonstrate that full anti-proliferative activities of the scabrosin esters, both the carboskeleton core as well as the ability to form the dithiol and/or the disulfide linkage of the epidithiopiperazine-2,5-dione are required. The presence of the epoxide rings on the scabrosin esters do not contribute to the observed biological activities. (C) 2004 Elsevier Ltd. All rights reserved.