benzyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate | 1143506-05-1

• 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: benzyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate
• 英文别名: benzyl (1S,4S,5R,9S,10S,13S,14R,15R)-14-hydroxy-15-(hydroxymethyl)-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1143506-05-1
• 化学式: C₂₈H₄₀O₄
• 分子量: 440.623
• InChiKey: PWSNDTWCAJMXKF-JVDMJLNVSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  556.5±40.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate 在 吡啶 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 ent-15-methylene-16-oxobeyeran-19-oic acid
  参考文献：
  名称：

  异甜菊醇衍生物及其制备与应用

  摘要：

  本发明公开了异甜菊醇衍生物及其制备与应用，异甜菊醇衍生物包括式I所示的化合物、式II所示的化合物；其中，代表是单键或双键；R1和R2分别独立的选自：氢原子、亚甲基和取代基为C1‑C10的胺烷基、能替代羰基或亚甲基的前体结构，如Mannich碱、亚胺盐等；其中，R3选自OR4OCOCHCHR5、OR4R6、NR4、OR4X⊕(Y)3Z⊙；R4选烃基、醚链、胺链；R5选自三氟甲基、苯基、苄基、吡啶基、呋喃基、吡咯基、吲哚基、胺乙基；R6选自H原子、青蒿琥酯基、苄基、式II的母核以形成二聚体；X选自P原子或N原子；选自甲基、乙基、异丙基、丁基、苯基；Z选自F、Cl、Br、I。

  公开号：

  CN108456240B
• 作为产物：
  描述：

  异甜菊醇 在 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate
  参考文献：
  名称：

  苯脒缀合将排出的潜在活性剂转化为针对耐药真菌的抗真菌剂

  摘要：

  真菌感染日益成为全球公共卫生问题，因此需要开发新型抗真菌药物。然而，许多潜在的抗真菌药物，特别是排出的潜在活性剂（EPAAs），由于其在细胞进入或外排泵排出方面的限制，常常被低估。在此，我们从 2322 个候选者中鉴定出 68 个 EPAAs 对白色念珠菌外排泵缺陷菌株具有活性，但对野生型菌株没有抑制活性。使用苯甲脒（BM）作为线粒体靶向弹头的新型结合策略，我们成功地将 EPAA 转化为有效的抗真菌剂，对抗各种紧急威胁的唑类抗性念珠菌菌株。在获得的EPAA-BM缀合物中，IS-2-BM (11)表现出优异的抗真菌活性，并且诱导的耐药性可以忽略不计。此外，IS-2-BM可防止生物膜形成，根除成熟生物膜，并在全身性念珠菌病小鼠模型中表现出优异的治疗效果。这些发现为增加发现更多抗真菌药物的可能性提供了一种有前景的策略。

  DOI：

  10.1021/acs.jmedchem.3c01068

文献信息

• Synthesis and Study of the Structure–Activity Relationship of Antiproliferative N-Substituted Isosteviol-Based 1,3-Aminoalcohols
  作者：Dániel Ozsvár、Noémi Bózsity、István Zupkó、Zsolt Szakonyi

  DOI：10.3390/ph17020262

  日期：——

  Starting from isosteviol, a series of diterpenoid 1,3-aminoalcohol derivatives were prepared via stereoselective transformations. The acid-catalysed hydrolysis and rearrangement of natural stevioside produced isosteviol, which was transformed into the key intermediate methyl ester. In the next step, an 1,3-aminoalcohol library was prepared by the reductive amination of the intermediate 3-hydroxyaldehyde

  以异甜菊醇为原料，通过立体选择性转化制备了一系列二萜1,3-氨基醇衍生物。天然甜菊苷经酸催化水解、重排生成异甜菊醇，并转化为关键中间体甲酯。下一步，通过两步合成中从异甜菊醇获得的中间体 3-羟基醛的还原胺化制备 1,3-氨基醇库。为了研究4位羧酸酯官能团的影响，将游离羧酸、苄酯和丙烯酰酯类似物制备为伸长衍生物，并与我们在该领域的早期结果进行比较。研究了化合物针对人类肿瘤细胞系（A2780、HeLa、MCF-7 和 MDA-MB-231）的抗增殖活性。在我们的初步研究中，具有N-苄基或(1H-咪唑-1-基)-丙基取代和苄基酯部分的1,3-氨基醇功能似乎对于可靠的抗增殖活性至关重要。获得的结果可能是进一步功能化以获得更有效的抗增殖二萜的良好起点。
• Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors
  作者：Ya Wu、Jing-Hua Yang、Gui-Fu Dai、Cong-Jun Liu、Guo-Qiang Tian、Wen-Yan Ma、Jing-Chao Tao

  DOI：10.1016/j.bmc.2009.01.017

  日期：2009.2

  Considerable interest has been attracted in isosteviol and its derivatives because of their large variety of pharmacological activities. In this project, a series of novel compounds containing hydroxyl, hydroxymethyl group and heteroatom-containing frameworks fused with isosteviol structure were synthesized and evaluated as alpha-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these isosteviol derivatives were capable of inhibiting in vitro alpha-glucosidase with moderate to good activities. Among them, indole derivative 15b exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent alpha-glucosidase inhibitors. (c) 2009 Published by Elsevier Ltd.
• Synthesis and biological evaluation of novel exo-methylene cyclopentanone tetracyclic diterpenoids as antitumor agents
  作者：Jing Li、Dayong Zhang、Xiaoming Wu

  DOI：10.1016/j.bmcl.2010.11.055

  日期：2011.1

  The structure of exo-methylene cyclopentanone, which exists in nature tetracyclic diterpenoids products, has been proved to be an innate group for the treatment of cancer and inflammation. In this letter, four different scaffolds of tetracyclic diterpenoids including the structure exo-methylene cyclopentanone were synthesized from steviol and isosteviol and evaluated in vitro for their antitumor activity against three human cancer lines. Compounds 1a, 1b, 2b and 3b showed significant cytotoxicity, particularly, tetracyclic diterpenoids 2b, 3b were identified as the most potent and selective anticancer agents superior to adriamycin with IC50 values of 0.9 mu M and 1.5 mu M, against Hep-G2 and MDA-MB-231 cell lines, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of cytotoxic effects of novel α-methylenelactone tetracyclic diterpenoids
  作者：Yao-fu Zeng、Jia-qiang Wu、Lian-yong Shi、Ke Wang、Bin Zhou、Yong Tang、Da-yong Zhang、Yang-chang Wu、Wei-yi Hua、Xiao-ming Wu

  DOI：10.1016/j.bmcl.2012.01.051

  日期：2012.3

  A series of tetracyclic diterpenoids bearing the alpha-methylenelactone group have been synthesized and screened for their in vitro anti-tumor activities against six human cancer cell lines. The results showed that compounds 1c, 2a and 2b exhibited significant cytotoxicity superior to the positive control doxorubicin hydrochloride against MDA-MB-231, K562 and HepG2 cell lines. In particular, compound 2b was identified as the most promising anticancer agent against HepG2 cells with IC50 value of 0.09 mu M. (c) 2012 Elsevier Ltd. All rights reserved.