9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one | 477952-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one
• 英文别名: (2R,6R,7R,10S,12R,13R,14R)-10,13-dihydroxy-4,4,7,17,18,18-hexamethyl-11-methylidene-3,5-dioxatetracyclo[12.3.1.02,6.07,12]octadec-1(17)-en-16-one
• CAS: 477952-08-2
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: HLFTVSGJYNXFIO-PXEYHYAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one 在 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氢氧化钾 、 四氧化锇 、 N-甲基吲哚酮 、 四丁基氟化铵 、 水 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 111.42h， 生成 2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-9α,10β-isopropylidenedioxy-11-taxen-13-one
  参考文献：
  名称：

  合成和2-抗肿瘤活性（米-取代的苯甲酰基）浆果赤霉素从taxinine III类似物

  摘要：

  由紫杉碱（日本紫杉叶的主要成分）制备2- m-叠氮基苯甲酰基和2- m-氯苯甲酰基浆果赤霉素III类似物。在这项研究中，观察到了新的从13-羟基迁移到4-羟基的乙酰基。评价了这些化合物的抗肿瘤活性。

  DOI：

  10.1016/s0040-4020(03)00048-6
• 作为产物：
  描述：

  9α,10β-dihydroxy-2α-acetoxy-5α-cinnamoyloxy-taxa-4(20),11-dien-13-one 在 氢氧化钾 、 4-甲基苯磺酸吡啶 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one
  参考文献：
  名称：

  An Efficient Conversion of Taxinine to Taxinine NN-1, an Anticancer Agent and a Modulator of Multidrug-Resistant Tumor Cells

  摘要：

  Taxinine NN-1 (1), which shows significant activities as a modulator of multidrug-resistant cancer cells and as an anticancer agent in an in vitro assay based on a HCC panel, was synthesized in order to obtain sufficient material for a higher order bioassay from easily available taxinine (2). The synthesis was achieved via intermediate 8, which was derived from 2 by the stepwise protection of a 9, 10-dihydroxyl group as acetonide and a 2-hydroxyl group as a MOM protecting group. The temporary elimination of a cinnamoyl group at C-5 of 8 and successive reduction of a C-13 carbonyl group of the resulting 9 gave 10 and the undesired 13-epimer 11. The latter was recycled to 9 by oxidation with MnO2. Stepwise acetylation and cinnamoylation at C-13 and C-5 of 10 and successive deprotection of the acetonide protecting group at C-9,10 of the resulting 13 gave diol 14. Diacetylation of 14 and deprotection of the MOM protecting group at C-2 of the resulting 15 gave 1. The overall yield of 1 was 45% in 11 steps from 2.

  DOI：

  10.1021/np020240n

文献信息

• An Efficient Conversion of Taxinine to Taxinine NN-1, an Anticancer Agent and a Modulator of Multidrug-Resistant Tumor Cells
  作者：Shujun Zhang、Jinlan Wang、Katutoshi Hirose、Masayoshi Ando

  DOI：10.1021/np020240n

  日期：2002.12.1

  Taxinine NN-1 (1), which shows significant activities as a modulator of multidrug-resistant cancer cells and as an anticancer agent in an in vitro assay based on a HCC panel, was synthesized in order to obtain sufficient material for a higher order bioassay from easily available taxinine (2). The synthesis was achieved via intermediate 8, which was derived from 2 by the stepwise protection of a 9, 10-dihydroxyl group as acetonide and a 2-hydroxyl group as a MOM protecting group. The temporary elimination of a cinnamoyl group at C-5 of 8 and successive reduction of a C-13 carbonyl group of the resulting 9 gave 10 and the undesired 13-epimer 11. The latter was recycled to 9 by oxidation with MnO2. Stepwise acetylation and cinnamoylation at C-13 and C-5 of 10 and successive deprotection of the acetonide protecting group at C-9,10 of the resulting 13 gave diol 14. Diacetylation of 14 and deprotection of the MOM protecting group at C-2 of the resulting 15 gave 1. The overall yield of 1 was 45% in 11 steps from 2.
• Synthesis and antitumor activity of 2-(m-substituted-benzoyl)baccatin III analogs from taxinine
  作者：Tohru Horiguchi、Takayuki Oritani、Hiromasa Kiyota

  DOI：10.1016/s0040-4020(03)00048-6

  日期：2003.2

  2-m-Azidobenzoyl and 2-m-chlorobenzoyl baccatin III analogs were prepared from taxinine, a major component in Japanese yew leaves. In this study, a novel acetyl migration from 13- to 4-hydroxyl group was observed. The antitumor activity of these compounds was evaluated.

  由紫杉碱（日本紫杉叶的主要成分）制备2- m-叠氮基苯甲酰基和2- m-氯苯甲酰基浆果赤霉素III类似物。在这项研究中，观察到了新的从13-羟基迁移到4-羟基的乙酰基。评价了这些化合物的抗肿瘤活性。

表征谱图