taxinine A | 18530-09-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: taxinine A
• 英文别名: [(1R,2R,3R,5S,8R,9R,10R)-9,10-diacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxo-2-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 18530-09-1
• 化学式: C₂₆H₃₆O₈
• 分子量: 476.567
• InChiKey: OQXJKHGIAZCMBX-SOIIJPRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  taxinine A 在 咪唑 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-O-deacetyl-5-O-triethylsilyl-taxinine A
  参考文献：
  名称：

  Modulation of multidrug resistance in tumor cells by taxinine derivatives

  摘要：

  Among a series of taxinine (1) and its designed derivatives (2 similar to 33), two taxoids (29 and 33) increased cellular accumulation of vincristine in multidrug-resistant tumor cells more potently than verapamil, while the activities of eight taxoids (11, 14 similar to 16, 22, and 30 similar to 32) were comparable with that of verapamil. These results reveal that some taxinine derivatives are good modifiers of multidrug resistance in tumor cells. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00009-8
• 作为产物：
  描述：

  taxinine 在 硫酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 以80%的产率得到taxinine A
  参考文献：
  名称：

  Modulation of multidrug resistance in tumor cells by taxinine derivatives

  摘要：

  Among a series of taxinine (1) and its designed derivatives (2 similar to 33), two taxoids (29 and 33) increased cellular accumulation of vincristine in multidrug-resistant tumor cells more potently than verapamil, while the activities of eight taxoids (11, 14 similar to 16, 22, and 30 similar to 32) were comparable with that of verapamil. These results reveal that some taxinine derivatives are good modifiers of multidrug resistance in tumor cells. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00009-8

文献信息

• Syntheses of Taxuspine C Derivatives as Functional Inhibitors of P-Glycoprotein, an ATP-Associated Cell-Membrane Transporter.
  作者：Magoichi SAKO、Hikokazu SUZUKI、Kosaku HIROTA

  DOI：10.1248/cpb.46.1135

  日期：——

  UV-Irradiation of taxinine and related compounds in acetonitrile induced a smooth transannulation between the C-3 and C-11 positions without any influence from the C-2, C-9 and C-10 substituents to give tetracyclic taxuspine C derivatives in almost quantitative yields. Photochemical transannular reaction of taxoids possessing a cinnamoyl group in the side-chain was accompanied by an E,Z-isomerization

  在乙腈中紫外线照射紫杉碱及相关化合物可诱导C-3和C-11位置之间平稳过渡，而不受C-2，C-9和C-10取代基的影响，从而得到几乎定量的四环紫杉烷C衍生物产量。在侧链上具有肉桂酰基的紫杉烷类化合物的光化学跨环反应伴随着肉桂酰基部分的E，Z-异构化。发现长春新碱（一种对癌症化疗有用的药物）在具有多重耐药性的卵巢癌细胞中的细胞蓄积最有效地增加了5-O-苯甲酰化的5-O-癸氨酰紫杉醇C的含量。这表明5-O-苯甲酰化的红豆杉C衍生物可能是有前途的P糖蛋白功能抑制剂，它可作为癌症化疗药物的ATP相关外排泵。
• Stereoselective epoxidation of 4(20)-exomethylene in taxinine derivatives and assignment of the epoxide orientation by NMR
  作者：Hirokazu Hosoyama、Hideyuki Shigemori、Yasuko In、Toshimasa Ishida、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4020(98)00018-0

  日期：1998.3

  Epoxidation of taxinine (1), taxinine A (2), and taxinine derivative 7 with m-chloroperbenzoic acid afforded the α-4(20)-epoxides selectively (α : β = 99 : 1), while epoxidation of taxinine derivatives 7 and 8 with dimethyldioxirane gave the β-4(20)-epoxides predominantly (α : β = 1 : 4∼5). The epoxide orientation was found to be assignable by magnitude of chemical shift differences between the geminal

  taxinine（环氧化1），taxinine A（2），和taxinine衍生物7与米，得到氯过苯甲酸的α-4（20） -环氧化物选择性（α：β = 99：1），而taxinine衍生物的环氧化7和8与二甲基二，得到β-4（20） -环氧化物主要（α：β = 1：4〜5）。发现环氧化物的取向可通过1 H NMR光谱中双环环氧质子之间的化学位移差异的大小来确定。1β-羟基浆果赤霉素I的相对立体化学（9通过X射线分析确定具有β-4（20）-环氧部分的），以提供环氧方向的有效分配。
• Occurrence of a new dimeric compound of 5-oxotaxinine A through Diels-Alder cycloaddition
  作者：Hirokazu Hosoyama、Hideyuki Shigemori、Yasuko In、Toshimasa Ishida、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4039(98)00146-4

  日期：1998.4

  Oxidation of taxinine A (1) with tetrapropylammonium perruthenate afforded 5-oxotaxinine A (2) which subsequently gave a new dimeric compound (3) through regio- and stereo-specific Diels-Alder cycloaddition. The relative stereostructure of 3 was established by spectral data and X-ray analysis.

  用过钌酸四丙基铵氧化紫杉碱A（1），得到5-氧代辛氨酸A（2），随后通过区域和立体特异性Diels-Alder环加成反应得到新的二聚化合物（3）。通过光谱数据和X射线分析建立了3的相对立体结构。
• Determination of the Stereochemistry of C-2’ and C-3’ Positions of Taxine NA-1 (2’-Hydroxytaxine II) by the Asymmetric Synthesis of the Reductive Degradation Product of Its Side Chain Moiety
  作者：Wanxia Tang、Masayoshi Ando、Hiroshi Minato、Mariko Ando

  DOI：10.3987/com-12-12480

  日期：——

  The reductive degradation of taxine NA-1 (2'-hydroxytaxine II) with n-Bu4NBH4 gave taxinine A and (-)-3-dimethylarnino-3-phenylpropane-1,2-diol (1) in addition to 11,12-dihydrotaxinine A. The relative stereochemistry of (-)-1 was identical with syn-3-dimethylamino-3-phenylpropane-1,2-diol, (+/-)-1b, which was synthesized from cis-2,3-epoxy-3-phenylpropan-1-ol, (+/-)-7. The absolute configuration of (-)-1 was certified by comparison of the specific optical rotation and the spectroscopic data of (-)-1 with those of (+)-1b and (-)-1b, which were enantioselectively synthesized by Sharp less asymmetric epoxidation reaction of cis-cinnamyl alcohol (6), respectively. As the result, the relative and absolute configuration of (-)-1 was same with that of (-)-1b possessing (2R, 35) configuration. Thus, the absolute configuration of the side chain of taxine NA-1 (2'-hydroxytaxine II) at C-2' and C-3' positions was determined to be (2'R, 3'S).
• Synthetic Studies Towards Taxol Analogs: Chemoselective Cleavage of C-5 Cinnamoyl Group in Taxane Group of Diterpenoids with Hydroxylamine
  作者：Yadagiri Bathini、Ronald G. Micetich、Mohsen Daneshtalab

  DOI：10.1080/00397919408010151

  日期：1994.6

  Taxane group of diterpenoids 2 and 3 which possess cinnamoyl moiety at C-5 position underwent selective cleavage to C-5 hydroxy compounds 4 and 5 on treatment with hydroxylamine. The resulting compounds were characterised based on their spectral data.