sordaricin | 51493-69-7

• 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: sordaricin
• 英文别名: (1R,3aR,4S,4aR,7R,7aR,8aS)-4-formyl-8a-(hydroxymethyl)-3-isopropyl-7-methyl-4,4a,5,6,7,7a,8,8a-octahydro-1,4-methano-s-indacene-3a(1H)-carboxylic acid；(1R,2S,4R,5R,8R,9S,11R)-9-formyl-2-(hydroxymethyl)-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid
• CAS: 51493-69-7
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: QIMCUSGGYZHVEF-VULLPXFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sordaricin 在 对甲苯磺酸 potassium carbonate 、 原甲酸三甲酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl (1R,3aR,4S,4aR,7R,7aR,8aS)-4-(1,3-dioxolan-2-yl)-8a-(hydroxymethyl)-3-isopropyl-7-methyl-4,4a,5,6,7,7a,8,8a-octahydro-1,4-methano-s-indacene-3a(1H)-carboxylate
  参考文献：
  名称：

  [EN] SORDARIN DERIVATIVES FOR PREVENTING OR TREATING INFECTIOUS DISEASES CAUSED BY PATHOGENIC MICROORGANISMS
  [FR] DÉRIVÉS DE SORDARINE POUR PRÉVENIR OU TRAITER DES MALADIES INFECTIEUSES CAUSÉES PAR DES MICRO-ORGANISMES PATHOGÈNES

  摘要：

  这项发明涉及一种新的索达林衍生物或其药用可接受的盐，该衍生物具有抗菌活性（特别是抗真菌活性），其制备方法，包含该衍生物的药物组合物，以及用于预防或治疗人类或动物传染性疾病的方法。

  公开号：

  WO2009131246A1
• 作为产物：
  描述：

  (3R,3aS,4R,7S,7aR,1'R,2'R,5'R)-3-methoxymethoxymethyl-3-[{2'-(1''-(methoxymethoxymethyl)vinyl)-5'-methylcyclopentyl}methyl]-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-one 在 六甲基磷酰三胺 、 manganese(IV) oxide 、 丙烷-1-硫醇 、 丁硫醇 、 sodium hydride 、 lithium,azanidylidenemethylidenecopper,2H-thiophen-2-ide 、 magnesium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 氘代甲苯 、 邻二氯苯 为溶剂， 反应 172.5h， 生成 sordaricin
  参考文献：
  名称：

  Total Synthesis of Sordaricin

  摘要：

  An enantioconvergent total synthesis of sordaricin (3), the diterpene aglycon of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton of the target molecule as a single regioisomer 30. A second approach employed a tandem cycloreversion/intramolecular [4 + 2] cycloaddition process to afford not only the desired product 30 but also significant quantities of the undesired regioisomer iso-30. An investigation into the reasons for the difference in regioselectivity between these two reactions revealed the intervention of a cycloreversion/cycloaddition pathway at elevated temperatures leading to the formation of iso-30. Experimental evidence supports the hypothesis that iso-30 is the more thermodynamically stable of the two regioisomers.

  DOI：

  10.1021/jo048199b

文献信息

• Synthesis of (−)-Sordarin
  作者：Shunsuke Chiba、Mitsuru Kitamura、Koichi Narasaka

  DOI：10.1021/ja060408h

  日期：2006.5.1

  synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed intramolecular allylation reaction resulting in the entire strained bicyclo[2.2.1]heptan-2-one framework of sordaricin (2); (iii) selective dihydroxylation of terminal

  (-)-sordarin (1) 的首次全合成利用以下关键反应完成：(i) Ag(I)-催化氧化自由基环化环丙醇衍生物生成双环 [5.3.0]decan-3-一具骷髅；(ii) Pd(0)-催化的分子内烯丙基化反应产生完整的双环[2.2.1]heptan-2-one骨架sordaricin (2)；(iii) 通过组合使用 OsO(4) 和 PhB(OH)(2) 选择性地二羟基化末端烯烃；(iv) 通过 4-甲氧基苯甲酰基的 1,3-嵌合辅助作用进行 β(1,2-顺式)-选择性糖苷化。
• Sordaricin antifungal agents
  作者：Claude A Quesnelle、Patrice Gill、Marco Dodier、Denis St. Laurent、Michael Serrano-Wu、Anne Marinier、Alain Martel、Charles E Mazzucco、Terry M Stickle、John F Barrett、Dolatrai M Vyas、Balu N Balasubramanian

  DOI：10.1016/s0960-894x(02)00937-x

  日期：2003.2

  organometallic addition onto a fully protected sordaricin aldehyde. The fungal growth inhibition profiles for these compounds were established and the results are presented here. The synthesis of homologated sordaricin as well as ether and ester derivatives is presented, and structural rearrangement products upon oxidation. These compounds were evaluated as agents to inhibit fungal growth.

  通过将有机金属加成到完全保护的苏达霉素醛上来制备基于苏达霉素的化合物。建立了这些化合物的真菌生长抑制曲线，并在此处显示了结果。介绍了合成的索达霉素以及醚和酯衍生物的合成，以及氧化后的结构重排产物。这些化合物被评估为抑制真菌生长的试剂。
• The Production of Novel Sordarin Analogues by Biotransformation.
  作者：RICHARD M. HALL、MICHAEL J. DAWSON、CAROL A. JONES、ANDREW D. ROBERTS、PHILIP J. SIDEBOTTOM、PAUL STEAD、NICK L. TAYLOR

  DOI：10.7164/antibiotics.54.948

  日期：——

  The biotransformation of the fungal protein synthesis inhibitor sordarin is reported. Nine taxonomically diverse organisms supported the isolation and identification of twelve modified products. The structural diversity of the biotransformation products observed and their value in supporting further chemistry is discussed.

  报告了真菌蛋白质合成抑制剂索达林的生物转化。九种不同分类的生物支持了十二种改性产物的分离和鉴定。本文讨论了所观察到的生物转化产物的结构多样性及其在支持进一步化学研究方面的价值。
• Novel thio derivatives of sordarin as antifungal agents
  申请人：——

  公开号：US20020035073A1

  公开（公告）日：2002-03-21

  The present invention relates to antifungal compounds having the structural formula: 1 and pharmaceutically acceptable salts, solvates and prodrugs thereof. The present invention further relates to pharmaceutical compositions containing said compound, or a pharmaceutically acceptable salt, solvate or prodrug thereof, for use in the treatment of a fungal infection in an animal host.

  本发明涉及具有结构式的抗真菌化合物： 1 及其药学上可接受的盐、溶液剂和原药。本发明还涉及含有所述化合物或其药学上可接受的盐、溶液剂或原药的药物组合物，用于治疗动物宿主的真菌感染。
• Synthesis and evaluation of novel pyrrolidinyl sordaricin derivatives as antifungal agents
  作者：Masami Arai、Tamako Harasaki、Takashi Fukuoka、Satoru Kaneko、Toshiyuki Konosu

  DOI：10.1016/s0960-894x(02)00534-6

  日期：2002.10

  N-Benzyl pyrrolidinyl sordaricin derivatives have been synthesized from cis-4-hydroxy-D-proline in a stereocontrolled manner. These compounds maintained moderate antifungal activity against several pathogenic fungal strains. Their MIC values against Candida albicans were in the range of 0.25-2 mug/mL. (C) 2002 Elsevier Science Ltd. All rights reserved.