catharanthine hydrochloride | 2645-61-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 依波格型生物碱
• 英文名称: catharanthine hydrochloride
• 英文别名: Catharanthine hydrochloride；methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate;hydrochloride
• CAS: 2645-61-6
• 化学式: C₂₁H₂₄N₂O₂*ClH
• 分子量: 372.895
• InChiKey: AVBOKMGDTOZFMW-GYMDHWDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.24
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  46.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  catharanthine hydrochloride 在 palladium on activated charcoal 盐酸 、 氢气 、 三氯化铁 、 聚甘氨酸 、 sodium chloride 作用下， 以 甲醇 为溶剂， 反应 5.17h， 生成 15',20'-dihydro-1-demethyl-16-dehydroxy-17-deacetoxyanhydrovinblastine
  参考文献：
  名称：

  Vinblastine-Type Antitumor Alkaloids:  A Method for Creating New C17 Modified Analogues

  摘要：

  DOI：

  10.1021/jo981269s

文献信息

• Inhibitors of tubulin polymerization: Synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III
  作者：Daniele Passarella、Alessandra Giardini、Bruno Peretto、Gabriele Fontana、Alessandro Sacchetti、Alessandra Silvani、Cristina Ronchi、Graziella Cappelletti、Daniele Cartelli、Jurgen Borlak、Bruno Danieli

  DOI：10.1016/j.bmc.2008.04.025

  日期：2008.6

  A series of novel hybrid compounds obtained by the attachment of anhydrovinblastine, vinorelbine, and vindoline to thiocolchicine, podophyllotoxin, and baccatin III are described. Two types of diacyl spacers are introduced. The influence of the hybrid compounds on tubulin polymerization is reported. The results highlight the importance of the length of the spacer. Immunofluorescence microscopy and

  描述了通过将脱水长春碱，长春瑞滨和长春碱与硫代秋水仙碱，鬼臼毒素和浆果赤霉素III连接而获得的一系列新型杂合化合物。介绍了两种类型的二酰基间隔基。报道了杂合化合物对微管蛋白聚合的影响。结果突出了间隔物的长度的重要性。具有最佳体外活性的化合物的免疫荧光显微镜和流式细胞术测量可能会破坏细胞中的微管网络并阻止适当的纺锤体设备的形成，从而导致细胞周期停滞在G2 / M期。在人肺癌细胞系A549中测试了新合成的化合物。
• Scott, A. Ian; Lee, Siu-Leung; Culver, Michael G., Heterocycles, 1981, vol. 15, # 2, p. 1257 - 1274
  作者：Scott, A. Ian、Lee, Siu-Leung、Culver, Michael G.、Wan, Winnie、Hirata, Toshifumi、et al.

  DOI：——

  日期：——
• Anodic Fragmentation of Catharanthine and Coupling with Vindoline. Formation of Anhydrovinblastine
  作者：Ibro Tabakovic、Esmir Gunic、Ivan Juranic

  DOI：10.1021/jo9621128

  日期：1997.2.1

  The anodic oxidation of catharanthine (Cath) in the presence of vindoline (Vind) performed in MeCN-Et(4)NClO(4) at a controlled potential yields (16'S)- and (16'R)-anhydrovinblastine (AVBL) in s 4.3:1 ratio. The favorable stereoselectivity found at room temperature is rationalized by proposing the coupling of generated dication 1a(++) and Vind at the electrode surface. The mechanism of the overall fragmentation/coupling reaction was studied using electrochemical techniques and the technique of homogeneous redox catalysis. It was concluded that the rate-determining step in the overall reaction is the first electron transfer leading to Cath(.+). MO calculations support the proposed mechanism and provide the evidence that C16-C21 bond fragmentation is a homolytic process.
• Vinblastine-Type Antitumor Alkaloids:  A Method for Creating New C17 Modified Analogues
  作者：Bruno Danieli、Giordano Lesma、Marisa Martinelli、Daniele Passarella、Alessandra Silvani、Bogomil Pyuskyulev、Mai Ngoc Tam

  DOI：10.1021/jo981269s

  日期：1998.11.1