Heptelidic acid chlorohydrin

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Heptelidic acid chlorohydrin
• 英文别名: heptelidic acid chlorhydrin；(5aS,6R,9S,9aS)-9-(chloromethyl)-9-hydroxy-6-isopropyl-1-oxo-1,3,5a,6,7,8,9,9a-octahydrobenzo[c]oxepine-4-carboxylic acid；chlorine heptelidic acid；(5aS,6R,9S,9aS)-9-(chloromethyl)-9-hydroxy-1-oxo-6-propan-2-yl-3,5a,6,7,8,9a-hexahydro-2-benzoxepine-4-carboxylic acid
• 化学式: C₁₅H₂₁ClO₅
• 分子量: 316.782
• InChiKey: BJGUEPXNQKBVBW-RTWAVKEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+)-萜烯七脂酸 在 溶剂黄146 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到Heptelidic acid chlorohydrin
  参考文献：
  名称：

  Anticancer activity of koningic acid and semisynthetic derivatives

  摘要：

  A screening program aimed at discovering novel anticancer agents based on natural products led to the selection of koningic acid (KA), known as a potent inhibitor of glycolysis. A method was set up to produce this fungal sesquiterpene lactone in large quantities by fermentation, thus allowing (i) an extensive analysis of its anticancer potential in vitro and in vivo and (ii) the semi-synthesis of analogues to delineate structure-activity relationships. KA was characterized as a potent, but non-selective cytotoxic agent, active under both normoxic and hypoxic conditions and inactive in the A549 lung cancer xenograft model. According to our SAR, the acidic group could be replaced to keep bioactivity but an intact epoxide is essential. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.004

文献信息

• Antiplasmodial compounds
  申请人：UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US11230569B2

  公开（公告）日：2022-01-25

  Novel compositions and methods for the treatment and prevention of malaria are disclosed herein.

  本文公开了用于治疗和预防疟疾的新型组合物和方法。
• METHODS OF TREATING TUMORS HAVING ELEVATED MCT1 EXPRESSION
  申请人：Whitehead Institute for Biomedical Research

  公开号：US20140142180A1

  公开（公告）日：2014-05-22

  In some aspects, compositions and methods useful for classifying tumor cells, tumor cell lines, or tumors according to predicted sensitivity to 3-bromopyruvate (3-BrPA) are provided. In some aspects, methods of identifying subjects with cancer who are candidates for treatment with 3-BrPA are provided. In some aspects, compositions useful for subjects with cancers that express increased levels of MCT1 are provided. In some aspects, methods of treating subjects with cancers that express increased levels of MCT1 are provided. In some aspects, methods of identifying anti-tumor agents the efficacy of which is at least in part dependent on transporter-mediated uptake are provided.
• NEW PRODUCT
  申请人：ALPHA BIOPESTICIDES LIMITED

  公开号：US20180146683A1

  公开（公告）日：2018-05-31

  The invention provides an agrochemical composition comprising: (a) one or more fatty acids or derivatives thereof; and (b) a strain, culture, culture filtrate, spores or mycelia of a species of a fungus or oomycete, or a metabolite produced by a species of a fungus or oomycete, which strain, culture, culture filtrate, spores, mycelia or metabolite directly or indirectly (i) inhibits the growth or reproduction of plant pathogens or (ii) kills plant pathogens. Also provided is a method for controlling fungi or oomycetes at a locus, a method for promoting growth in a plant and a method for controlling nematodes at a locus.
• ANTIPLASMODIAL COMPOUNDS
  申请人：UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US20200115415A1

  公开（公告）日：2020-04-16

  Novel compositions and methods for the treatment and prevention of malaria are disclosed herein.
• Anticancer activity of koningic acid and semisynthetic derivatives
  作者：Nicolas J. Rahier、Nicolas Molinier、Christophe Long、Sunil Kumar Deshmukh、Abhijeet S. Kate、Prafull Ranadive、Shilpa Amit Verekar、Mangesh Jiotode、Rahul R. Lavhale、Pradipta Tokdar、Arun Balakrishnan、Samuel Meignan、Céline Robichon、Bruno Gomes、Yannick Aussagues、Arnaud Samson、François Sautel、Christian Bailly

  DOI：10.1016/j.bmc.2015.04.004

  日期：2015.7

  A screening program aimed at discovering novel anticancer agents based on natural products led to the selection of koningic acid (KA), known as a potent inhibitor of glycolysis. A method was set up to produce this fungal sesquiterpene lactone in large quantities by fermentation, thus allowing (i) an extensive analysis of its anticancer potential in vitro and in vivo and (ii) the semi-synthesis of analogues to delineate structure-activity relationships. KA was characterized as a potent, but non-selective cytotoxic agent, active under both normoxic and hypoxic conditions and inactive in the A549 lung cancer xenograft model. According to our SAR, the acidic group could be replaced to keep bioactivity but an intact epoxide is essential. (C) 2015 Elsevier Ltd. All rights reserved.