(13α,14β,17α,20S)-tirucall-7-ene-3β,23,24,25-tetrol | 78739-39-6

• 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: (13α,14β,17α,20S)-tirucall-7-ene-3β,23,24,25-tetrol
• 英文别名: 3S,23R,24S,25-tetrahydroxytirucall-7-ene；piscidinol B；hispidol B；hispidol-B；(3S,4R,6S)-6-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-2,3,4-triol
• CAS: 78739-39-6
• 化学式: C₃₀H₅₂O₄
• 分子量: 476.74
• InChiKey: MVWLZBQPRMCRKT-ZAVAKTSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-二甲基琥珀酸酐 、 (13α,14β,17α,20S)-tirucall-7-ene-3β,23,24,25-tetrol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以8.3%的产率得到(13α,14β,17α,20S)-25-hydroxytirucall-7-en-3β,23,24-tri-(3’,3’-dimethyl)succinate
  参考文献：
  名称：

  Synthesis of piscidinol A derivatives and their ability to inhibit HIV-1 protease

  摘要：

  Four types of piscidinol A derivatives were synthesized and evaluated their ability to inhibit HIV-1 protease to understand their structure-activity relationships. Of these tirucallane-type triterpene derivatives, an A-seco derivative (1b) moderately inhibited human immunodeficiency virus (HIV) protease (IC50 38.2M). The 2,2-dimethyl succinic acid (DMS) acylated tirucallane derivatives (4b, 6a, and 7b, 50100M). These findings indicated that the 2,3-seco-2,3-dioic acid (1b) and DMS-acylated tirucallane-type derivatives preferably inhibited HIV viral protease.

  DOI：

  10.1080/10286020.2015.1084505
• 作为产物：
  描述：

  匹西狄醇 A 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以75.3%的产率得到(13α,14β,17α,20S)-tirucall-7-ene-3β,23,24,25-tetrol
  参考文献：
  名称：

  Synthesis of piscidinol A derivatives and their ability to inhibit HIV-1 protease

  摘要：

  Four types of piscidinol A derivatives were synthesized and evaluated their ability to inhibit HIV-1 protease to understand their structure-activity relationships. Of these tirucallane-type triterpene derivatives, an A-seco derivative (1b) moderately inhibited human immunodeficiency virus (HIV) protease (IC50 38.2M). The 2,2-dimethyl succinic acid (DMS) acylated tirucallane derivatives (4b, 6a, and 7b, 50100M). These findings indicated that the 2,3-seco-2,3-dioic acid (1b) and DMS-acylated tirucallane-type derivatives preferably inhibited HIV viral protease.

  DOI：

  10.1080/10286020.2015.1084505

文献信息

• Antiplasmodial and cytotoxic activities of the constituents of Turraea robusta and Turraea nilotica
  作者：Beatrice N. Irungu、Nicholas Adipo、Jennifer A. Orwa、Francis Kimani、Matthias Heydenreich、Jacob O. Midiwo、Per Martin Björemark、Mikael Håkansson、Abiy Yenesew、Máté Erdélyi

  DOI：10.1016/j.jep.2015.08.039

  日期：2015.11

  ETHNOPHARMACOLOGICAL RELEVANCE Turraea robusta and Turraea nilotica are African medicinal plants used for the treatment of a wide variety of diseases, including malaria. The genus Turraea is rich in limonoids and other triterpenoids known to possess various biological activities. MATERIALS AND METHODS From the stem bark of T. robusta six compounds, and from various parts of T. nilotica eleven compounds were

  族裔药理关系强壮龙虾和尼罗罗非鱼是用于治疗包括疟疾在内的多种疾病的非洲药用植物。Turraea属富含柠檬苦素和其他三萜类化合物，已知具有各种生物活性。材料和方法从罗汉果茎皮中分离出六种化合物，从尼罗罗非鱼的各个部位中分离出11种化合物，方法是采用色谱技术。使用NMR和MS阐明了分离的化合物的结构，同时通过X射线晶体学确定了分离的化合物之一的香豆素F的相对构型。使用半自动微量稀释技术测定粗提物和分离出的成分对恶性疟原虫D6和W2菌株的抗血浆活性，该技术可测量提炼物抑制（G-（3）H掺入的能力，其中G是鸟嘌呤）次黄嘌呤进入疟原虫。评估了粗提物及其分离成分对哺乳动物细胞系非洲猴肾（vero），小鼠乳腺癌（4T1）和人喉癌（HEp2）的细胞毒性。结果提取物表现出良好至中等的抗疟原虫活性，其中强壮罗非鱼茎皮提取物还对4T1和HEp2细胞具有细胞毒性（IC50 <10μg/ ml）。从这些提取物中分离
• GENE NETWORK-BASED METHOD FOR CONFIRMING DRUG ACTION
  申请人：Tsinghua University

  公开号：EP2369493A1

  公开（公告）日：2011-09-28

  The invention provides a network-based method for confirming drug action(drug effect, synergistic reaction). The method be carried out by mapping a first drug genes/gene products subset and a second genes/gene products subset in a gene network. The second genes/gene products subset can be a second drug genes/gene products subset or a biological process genes/gene products subset. The invention also provides a tool for pre-clinical drug screening.

  本发明提供了一种基于网络的确认药物作用（药物效应、协同反应）的方法。该方法通过在基因网络中绘制第一药物基因/基因产物子集和第二基因/基因产物子集来实现。第二基因/基因产物子集可以是第二药物基因/基因产物子集，也可以是生物过程基因/基因产物子集。本发明还为临床前药物筛选提供了一种工具。
• Triterpenes from Simaba multiflora
  作者：Munehisa Arisawa、Akio Fujita、Naokata Morita、Philip J. Cox、R. Alan Howie、Geoffrey A. Cordell

  DOI：10.1016/s0031-9422(00)82492-9

  日期：1987.1
• Triterpenoids from Walsura piscidia
  作者：T.R. Govindachari、G.N. Krishna Kumari、G. Suresh

  DOI：10.1016/0031-9422(94)00851-j

  日期：1995.5

  Piscidinol F, a new apotirucallane, has been isolated from the leaves of Walsura piscidia in addition to the other piscidinols. The side chain configuration of piscidinol B has been established from H-1 NMR data.
• [EN] GENE NETWORK-BASED METHOD FOR CONFIRMING DRUG ACTION<br/>[FR] PROCÉDÉ SELON UN RÉSEAU DE GÈNES POUR CONFIRMER L'ACTION D'UN MÉDICAMENT
  申请人：UNIV TSINGHUA

  公开号：WO2010066150A9

  公开（公告）日：2011-07-21

  [EN] The invention provides a network-based method for confirming drug action(drug effect?synergistic reaction). The method be carried out by mapping a first drug genes/gene products subset and a second genes/gene products subset in a gene network. The second genes/gene products subset can be a second drug genes/gene products subset or a biological process genes/gene products subset. The invention also provides a tool for pre-clinial drug screening.
  [FR] L'invention porte sur un procédé selon un réseau pour confirmer l'action d'un médicament (effet de médicament, réaction synergique). Le procédé peut être effectué par la mise en correspondance d'un premier sous-ensemble de gènes/produits de gène de médicament et d'un second sous-ensemble de gènes/produits de gène dans un réseau de gènes. Le second sous-ensemble de gènes/produits de gène peut être un second sous-ensemble de gènes/produits de gène de médicament ou un sous-ensemble de gènes/produits de gène de processus biologique. L'invention porte également sur un outil de criblage avant la partie clinique des études de médicament.