methyl 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-4-hydroxybenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-4-hydroxybenzoate
• 英文别名: (–)-dictyoceratin-C；ent-dictyoceratin-C；dictyoceratin C；dictyoceratin-C
• 化学式: C₂₃H₃₂O₃
• 分子量: 356.505
• InChiKey: WNSIKCDGFAFGBP-DQOBCGMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-溴-3-甲基-2-丁烯 、 methyl 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-4-hydroxybenzoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以1.0 mg的产率得到17-O-isoprenyldictyoceratin-C
  参考文献：
  名称：

  Marine Sesquiterpenoids that Inhibit the Lyase Activity of DNA Polymerase β

  摘要：

  Bioassay-directed fractionation of an extract of the marine species Spongia sp. led to the discovery of the new sesquiterpenoid derivative 17-O-isoprenyldictyoceratin-C (1), the known sesquiterpenoid derivative dictyoceratin-C (2), and the sesquiterpenoid quinone ilimaquinone (3), in addition to the nucleoside 2'-deoxyuridine. The structure of the new compound I was determined on the basis of spectroscopic methods and by conversion of dictyoceratin-C (2) to 1.

  DOI：

  10.1021/np049849+
• 作为产物：
  描述：

  4-羟基-3-甲基苯甲酸 在 盐酸 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 偶氮二异丁腈 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 147.42h， 生成 methyl 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-4-hydroxybenzoate
  参考文献：
  名称：

  Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge

  摘要：

  Total syntheses of (+)-dictyoceratin-C (1) and (+)-dictyoceratin-A (smenospondiol) (2), hypoxia-selective growth inhibitors isolated from marine sponge, were executed. The absolute stereochemistry of the each compound was determined through the enantioselective total syntheses of them. It revealed that the unnatural enantiomers of them also exhibited the hypoxia-selective growth inhibitory activity against human prostate cancer DU-145 cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.021

文献信息

• NOVEL USE OF SESQUITERPENE DERIVATIVE
  申请人：Kookmin University Industry Academy Cooperation Foundation

  公开号：EP3482750A1

  公开（公告）日：2019-05-15

  The present disclosure relates to a novel use of a sesquiterpene derivative, more particularly to a composition for preventing, improving or treating macular degeneration or macular edema caused by vascular leakage in the eye, the composition containing a sesquiterpene derivative compound represented by Chemical Formula 1 of the present disclosure or a pharmaceutically acceptable salt thereof as an active ingredient. Whereas the intraocular disease-related treating agents available in the market should be injected directly into the vitreous cavity, thus causing pain and side effects, the sesquiterpene derivative compound of the present disclosure is delivered to the target tissue (eye) via different administration routes (oral, intraperitoneal, etc.) other than the intravitreal route. Accordingly, the sesquiterpene derivative compound provides excellent therapeutic effect without being restricted by the administration routes.

  本公开涉及倍半萜衍生物的一种新用途，更具体地说，涉及一种用于预防、改善或治疗由眼部血管渗漏引起的黄斑变性或黄斑水肿的组合物，该组合物含有本公开化学式 1 所代表的倍半萜衍生物化合物或其药学上可接受的盐作为活性成分。市场上与眼内疾病相关的治疗药物应直接注射到玻璃体腔内，因此会引起疼痛和副作用，而本公开的倍半萜衍生物化合物可通过不同的给药途径（口服、腹腔注射等）给药到目标组织（眼睛），而非玻璃体腔内途径。因此，倍半萜衍生物化合物不受给药途径的限制，可提供极佳的治疗效果。
• Use of sesquiterpene derivative
  申请人：KOOKMIN UNIVERSITY INDUSTRY ACADEMY COOPERATION FOUNDATION

  公开号：US10918625B2

  公开（公告）日：2021-02-16

  The present disclosure relates to a novel use of a sesquiterpene derivative, more particularly to a composition for preventing, improving or treating macular degeneration or macular edema caused by vascular leakage in the eye, the composition containing a sesquiterpene derivative compound represented by Chemical Formula 1 of the present disclosure or a pharmaceutically acceptable salt thereof as an active ingredient. Whereas the intraocular disease-related treating agents available in the market should be injected directly into the vitreous cavity, thus causing pain and side effects, the sesquiterpene derivative compound of the present disclosure is delivered to the target tissue (eye) via different administration routes (oral, intraperitoneal, etc.) other than the intravitreal route. Accordingly, the sesquiterpene derivative compound provides excellent therapeutic effect without being restricted by the administration routes.

  本公开涉及倍半萜衍生物的一种新用途，更具体地说，涉及一种用于预防、改善或治疗由眼部血管渗漏引起的黄斑变性或黄斑水肿的组合物，该组合物含有本公开化学式 1 所代表的倍半萜衍生物化合物或其药学上可接受的盐作为活性成分。市场上与眼内疾病相关的治疗药物应直接注射到玻璃体腔内，因此会引起疼痛和副作用，而本公开的倍半萜衍生物化合物可通过不同的给药途径（口服、腹腔注射等）给药到目标组织（眼睛），而非玻璃体腔内途径。因此，倍半萜衍生物化合物不受给药途径的限制，可提供极佳的治疗效果。
• Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge
  作者：Yuji Sumii、Naoyuki Kotoku、Akinori Fukuda、Takashi Kawachi、Yuta Sumii、Masayoshi Arai、Motomasa Kobayashi

  DOI：10.1016/j.bmc.2015.01.021

  日期：2015.3

  Total syntheses of (+)-dictyoceratin-C (1) and (+)-dictyoceratin-A (smenospondiol) (2), hypoxia-selective growth inhibitors isolated from marine sponge, were executed. The absolute stereochemistry of the each compound was determined through the enantioselective total syntheses of them. It revealed that the unnatural enantiomers of them also exhibited the hypoxia-selective growth inhibitory activity against human prostate cancer DU-145 cells. (C) 2015 Elsevier Ltd. All rights reserved.
• Marine Sesquiterpenoids that Inhibit the Lyase Activity of DNA Polymerase β
  作者：Shugeng Cao、Zhijie Gao、Shannon J. Thomas、Sidney M. Hecht、John S. Lazo、David G. I. Kingston

  DOI：10.1021/np049849+

  日期：2004.10.1

  Bioassay-directed fractionation of an extract of the marine species Spongia sp. led to the discovery of the new sesquiterpenoid derivative 17-O-isoprenyldictyoceratin-C (1), the known sesquiterpenoid derivative dictyoceratin-C (2), and the sesquiterpenoid quinone ilimaquinone (3), in addition to the nucleoside 2'-deoxyuridine. The structure of the new compound I was determined on the basis of spectroscopic methods and by conversion of dictyoceratin-C (2) to 1.