(2S,3S,4S,4aR)-3,4,7-trihydroxy-6-oxo-2,3,4,4a,5,6-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl acetate | 1019642-58-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: (2S,3S,4S,4aR)-3,4,7-trihydroxy-6-oxo-2,3,4,4a,5,6-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl acetate
• 英文别名: acetic acid 3,4,7-trihydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxol[4,5-j]phenanthridin-2-yl ester；[(2S,3S,4S,4aR)-3,4,7-trihydroxy-6-oxo-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-2-yl] acetate
• CAS: 1019642-58-0
• 化学式: C₁₆H₁₅NO₈
• 分子量: 349.297
• InChiKey: APFGDAWZIPFINP-MBGOOHRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  acetic acid 7-acetoxy-3,4-dihydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxol[4,5-j]phenanthridin-2-yl ester 在 吡啶 、 水 作用下， 反应 2.0h， 以66%的产率得到(2S,3S,4S,4aR)-3,4,7-trihydroxy-6-oxo-2,3,4,4a,5,6-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl acetate
  参考文献：
  名称：

  ISOCARBOSTYRIL ALKALOID DERIVATIVES HAVING ANTI-PROLIFERATIVE AND ANTI-MIGRATORY ACTIVITIES

  摘要：

  揭示了具有抗增殖和抗迁移活性的异喹啉生物碱衍生物。具体来说，公开了符合以下化学式(I)或(II)的化合物，以及其立体异构体、互变异构体、消旋体、前药、代谢物、药学上可接受的盐和/或溶剂，这些化合物在癌症的治疗和预防中很有用。还公开了制备方法。

  公开号：

  US20100076005A1

文献信息

• Sequential enzymatic and electrochemical functionalization of bromocyclohexadienediols: Application to the synthesis of (−)-conduritol C
  作者：Juana Goulart Stollmaier、Tomáš Hudlický

  DOI：10.1016/j.tet.2020.130924

  日期：2020.2

  regiochemistry when compared to the chemical epoxidation with m-CPBA, but with the unexpected formation of bromoconduritol-C, an important intermediate whose electrochemical reduction led to the synthesis of (−)-conduritol-C. Experimental and spectral data are provided for all new compounds.

  由溴苯的微生物氧化获得的顺式-二烯二醇用作化学酶乙酰化和脂肪酶环氧化的底物。模型研究表明乙酰化的区域化学是溶剂依赖性的。与使用m -CPBA进行化学环氧化相比，化学酶促环氧化遵循预期的区域化学反应，但是意外地形成了溴conduritol-C，这是一种重要的中间体，其电化学还原作用导致了（-）-conduritol-C的合成。提供了所有新化合物的实验和光谱数据。
• Structure−Activity Relationship Analysis of Novel Derivatives of Narciclasine (an <i>Amaryllidaceae</i> Isocarbostyril Derivative) as Potential Anticancer Agents
  作者：Laurent Ingrassia、Florence Lefranc、Janique Dewelle、Laurent Pottier、Véronique Mathieu、Sabine Spiegl-Kreinecker、Sébastien Sauvage、Mohamed El Yazidi、Mischaël Dehoux、Walter Berger、Eric Van Quaquebeke、Robert Kiss

  DOI：10.1021/jm8013585

  日期：2009.2.26

  Narciclasine (1) is a plant growth regulator that has been previously demonstrated to be proapoptotic to cancer cells at high concentrations (>= 1 mu M). Data generated in the present study show that narciclasine displays potent antitumor effects in apoptosis-resistant as well as in apoptosis-sensitive cancer cells by impairing the organization of the actin cytoskeleton in cancer cells at concentrations that are not cytotoxic (IC50 values of 30-90 nM). The current study further revealed that any chemical modification to the narciclasine backbone generally led to compounds of variable stability, weaker activity, or even the complete loss of antiproliferative effects in vitro. However, one hemisynthetic derivative of narciclasine, compound 7k, demonstrated by both the intravenous and oral routes higher in vivo antitumor activity in human orthotopic 4, glioma models in mice when compared to narciclasine at nontoxic doses. Narciclasine and compound 7k may therefore be of potential use to combat brain tumors.
• [EN] NEW ISOCARBOSTYRIL ALKALOID DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'ISOCARBOSTYRYL ALCALOÏDE
  申请人：UNIBIOSCREEN SA

  公开号：WO2008043846A2

  公开（公告）日：2008-04-17

  [EN] The present invention relates to novel isocarbostyril alkaloid derivatives having an anti-proliferative and anti-migratory activities, in particular to compounds of formula (I) or (II), stereoisomers, tautomers, racemates, prodrugs, metabolites thereof, or a pharmaceutically acceptable salt and/or solvate thereof, wherein R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ have the same meaning as that defined in the claims. The present invention also relates to a method for the preparation of said compounds, to compositions, in particular pharmaceuticals, comprising such compounds, and to uses of such compounds in the treatment and prophylaxis of cancer.
  [FR] La présente invention concerne de nouveaux dérivés d'isocarbostyryl alcaloïde présentant des activités antiprolifératives et anti-migratoires, en particulier des composés représentés par la formule (I) ou (II), des stéréo-isomères, des tautomères, des racémates, des promédicaments, des métabolites de ceux-ci, ou un sel et/ou un solvate de ceux-ci acceptable du point de vue pharmaceutique, où R¹, R², R³, R⁴, R⁵, R⁶, et R⁷ ont la même signification que celle qui est définie dans les revendications. La présente invention porte également sur un procédé pour la préparation desdits composés, sur des compositions, en particulier des compositions pharmaceutiques comportant de tels composés, et sur des utilisations de tels composés dans le traitement et la prophylaxie du cancer.