renieramycin W | 1178895-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: renieramycin W
• 英文别名: [(1R,2S,10R,12R,13S)-12-cyano-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),6,15(20),17-tetraen-10-yl]methyl (E)-2-methylbut-2-enoate
• CAS: 1178895-11-8
• 化学式: C₃₁H₃₃N₃O₈
• 分子量: 575.618
• InChiKey: QOGBZZDZYZICFV-CJKYZTOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (E)-2-甲基-2-丁烯酰氯 、 jorunnamycin A 以 乙醚 、 二氯甲烷 为溶剂， 反应 66.0h， 以31%的产率得到renieramycin W
  参考文献：
  名称：

  Chemistry of renieramycins. Part 13: Isolation and structure of stabilized renieramycin type derivatives, renieramycins W–Y, from Philippine blue sponge Xestospongia sp., pretreated with potassium cyanide

  摘要：

  Three new bistetrahydroisoquinoline marine natural products, renieramycins W (1w), X (1x), and Y (1y), along with two known renieramycins M (1m) and T (1t), were isolated from the pretreated Philippine blue sponge Xestospongia sp. with KCN and their structures were elucidated by comparing their spectral data with those of 1m, 1t, and N-acetylsafracin B (11). Renieramycins W (1w) and X (1x) are the first examples of tiglic acid ester derivatives at the C-1 side chain. Renieramycin Y (1y) possesses a characteristic substitution pattern in A-ring and isolation of it from marine organism strongly evidences to link the possible precursor 3-hydroxy-5-methyl-O-methyltyrosine with both renieramycin and ecteinascidin marine natural products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.067

文献信息

• Chemistry of renieramycins. Part 8: Synthesis and cytotoxicity evaluation of renieramycin M–jorunnamycin A analogues
  作者：Kornvika Charupant、Naomi Daikuhara、Emi Saito、Surattana Amnuoypol、Khanit Suwanborirux、Takashi Owa、Naoki Saito

  DOI：10.1016/j.bmc.2009.05.009

  日期：2009.7

  Twenty-four ester analogues of renieramycin M (1m) were prepared from jorunnamycin A (3a), which was easily transformed from marine natural 1m in three steps. These analogues, along with 1m itself, cyanojorumycin (2b), and jorunnamycins A (3a) and C (3b), were evaluated in vitro for cytotoxicity by measuring IC50 values through the 3-(4,5-dimethyltriazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay using human HCT116 colon carcinoma and MDA-MB-435 breast carcinoma cell lines. Nitrogen-containing heterocyclic ester derivatives 9a-f showed similar in vitro cytotoxicity to 1m, whereas the other derivatives were slightly less cytotoxic than 1m. 2'-Pyridinecarboxylic acid ester derivative (9c) exhibited a threefold increase in cytotoxicity relative to 1m. (C) 2009 Elsevier Ltd. All rights reserved.
• Chemistry of renieramycins. Part 13: Isolation and structure of stabilized renieramycin type derivatives, renieramycins W–Y, from Philippine blue sponge Xestospongia sp., pretreated with potassium cyanide
  作者：Mari Tatsukawa、Louvy Lynn C. Punzalan、Hilbert D.S. Magpantay、Irene M. Villaseñor、Gisela P. Concepcion、Khanit Suwanborirux、Masashi Yokoya、Naoki Saito

  DOI：10.1016/j.tet.2012.06.067

  日期：2012.9

  Three new bistetrahydroisoquinoline marine natural products, renieramycins W (1w), X (1x), and Y (1y), along with two known renieramycins M (1m) and T (1t), were isolated from the pretreated Philippine blue sponge Xestospongia sp. with KCN and their structures were elucidated by comparing their spectral data with those of 1m, 1t, and N-acetylsafracin B (11). Renieramycins W (1w) and X (1x) are the first examples of tiglic acid ester derivatives at the C-1 side chain. Renieramycin Y (1y) possesses a characteristic substitution pattern in A-ring and isolation of it from marine organism strongly evidences to link the possible precursor 3-hydroxy-5-methyl-O-methyltyrosine with both renieramycin and ecteinascidin marine natural products. (C) 2012 Elsevier Ltd. All rights reserved.