dregamine | 2299-26-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 沃巴桑生物碱
• 英文名称: dregamine
• 英文别名: 20-Epitabernemontanine；methyl (1S,14S,15R,18S)-15-ethyl-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate
• CAS: 2299-26-5
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: FFVRRQMGGGTQRH-YWKPPDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dregamine 生成 vincadifformin
  参考文献：
  名称：

  BENARDELLI, GIOVANNI

  摘要：

  DOI：
• 作为产物：
  描述：

  vobasine 生成 dregamine 、 tabernaemontanine
  参考文献：
  名称：

  Terpenoid indole alkaloid biotransformation capacity of suspension cultures of Tabernaemontana divaricata

  摘要：

  Two cell lines of Tabernaemontana divaricata derived from the same suspension culture were compared with respect to their biotransformation capacity. One is a high indole alkaloid-producing culture which accumulated mainly O-acetylvallesamine. The other cell line biosynthesizes terpehoid indole alkaloids in much lower amounts. Both cell lines were cultured in medium containing either conopharyngine, coronaridine, vobasine or tabersonine. Chemical breakdown was followed in fresh and used culture medium in the absence of cell culture. All the alkaloids investigated underwent chemical transformation. Most of the biotransformation products accumulated by the cultures have been reported to occur in intact plants. Since all the alkaloids added were transformed in the same way by both cultures, the two cell lines seem to have the same biotransformation potential.

  DOI：

  10.1016/s0031-9422(00)90584-3

文献信息

• [EN] NEW PHARMACEUTICAL COMPOUNDS, METHODS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS PHARMACEUTIQUES, LEURS MÉTHODES ET UTILISATIONS
  申请人：UNIV DO PORTO

  公开号：WO2022053998A1

  公开（公告）日：2022-03-17

  The present disclosure relates to novel compounds according to general Formula I or a pharmaceutically acceptable acid or base addition salts, hydrate, solvate, N-oxide, stereo chemically isomer forms, in particular diastereoisomer, enantiomer or atropisomers, or mixtures thereof, a polymorph or ester thereof. The present disclosure also relates to a pharmaceutical composition comprising a compound or prodrug thereof of Formula I for use in the treatment of conditions influenced by homologous recombination DNA repair pathway and wild-type, mutant and other BRCA1 and/or BRCA2 deficiencies, namely therapy or treatment of cancer.

  本公开涉及根据通用式I或其药学上可接受的酸或碱加合物盐、水合物、溶剂合物、N-氧化物、立体化学异构体形式，特别是对映异构体、对映体或旋光异构体或其混合物、多晶形或酯类的新化合物。本公开还涉及包括式I化合物或其前药的药物组合物，用于治疗受同源重组DNA修复途径和野生型、突变型和其他BRCA1和/或BRCA2缺陷影响的疾病，即癌症的治疗。
• Monoterpene indole alkaloid hydrazone derivatives with apoptosis inducing activity in human HCT116 colon and HepG2 liver carcinoma cells
  作者：Angela Paterna、Pedro M. Borralho、Sofia E. Gomes、Silva Mulhovo、Cecília M.P. Rodrigues、Maria-José U. Ferreira

  DOI：10.1016/j.bmcl.2015.06.084

  日期：2015.9

  The derivatization of dregamine (1) and tabernaemontanine (2), two epimeric monoterpene indole alkaloids isolated from the methanol extract of the roots of Tabernaemontana elegans, with several hydrazines and hydroxylamine gave rise to ten new derivatives (3-12). Their structures were assigned by spectroscopic methods, including 2D NMR experiments. The compounds were tested for their ability to induce apoptosis in HCT116 colon and HepG2 liver cancer cells. Firstly, the cytotoxicity of all compounds (1-12) was evaluated in both cell lines by the MTS assay. The most active compounds (6, 9, 10) along with 1 and 2 were further investigated for their apoptosis induction capability by Guava ViaCount flow cytometry assays, nuclear morphology evaluation by Hoechst staining, and caspase-3/7 activity assays. Compounds 9 and 10 showed promising apoptosis induction profile, displaying higher activities than 5-fluorouracil, the mainstay in colon cancer treatment. (C) 2015 Elsevier Ltd. All rights reserved.