(S)-2-((3R,3aR,5aR,5bR,8S,9aS,17aS,17bR)-8-(methoxymethoxy)-3a,5b-dimethyl-11,16-dioxo-2,3,3a,4,5,5a,5b,6,7,8,9,11,16,17b-tetradecahydro-1H-9a,17a-ethenobenzo[c]cyclopenta[h]phthalazino[2,3-a]cinnolin-3-yl)propanal | 358681-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-2-((3R,3aR,5aR,5bR,8S,9aS,17aS,17bR)-8-(methoxymethoxy)-3a,5b-dimethyl-11,16-dioxo-2,3,3a,4,5,5a,5b,6,7,8,9,11,16,17b-tetradecahydro-1H-9a,17a-ethenobenzo[c]cyclopenta[h]phthalazino[2,3-a]cinnolin-3-yl)propanal
• CAS: 358681-36-4
• 化学式: C₃₂H₄₀N₂O₅
• 分子量: 532.68
• InChiKey: SUJMNPUPCPUCAG-XEAUFJIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  79.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((3R,3aR,5aR,5bR,8S,9aS,17aS,17bR)-8-(methoxymethoxy)-3a,5b-dimethyl-11,16-dioxo-2,3,3a,4,5,5a,5b,6,7,8,9,11,16,17b-tetradecahydro-1H-9a,17a-ethenobenzo[c]cyclopenta[h]phthalazino[2,3-a]cinnolin-3-yl)propanal 在 lithium aluminium tetrahydride 、 diamide 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-2-((3S,9S,10R,13R,14R,17R)-3-Methoxymethoxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-heptan-3-ol
  参考文献：
  名称：

  Synthesis and evaluation of 4-deacetoxyagosterol A as an MDR-modulator

  摘要：

  4-Deacetoxyagosterol A was synthesized from ergosterol by utilizing reductive regioselective epoxy cleavage as a key reaction. This synthesized congener of agosterol A, a spongean MDR-modulator, showed similar MDR-modulating activity against KB CV-60 cells overexpressing MRP. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00502-3
• 作为产物：
  描述：

  (1S,2R,5R,6R,9R,10R,13S,15S)-5-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-13-(methoxymethoxy)-6,10-dimethyl-16,25-diazaheptacyclo[13.10.2.01,9.02,6.010,15.016,25.018,23]heptacosa-18,20,22,26-tetraene-17,24-dione 在 吡啶 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-2-((3R,3aR,5aR,5bR,8S,9aS,17aS,17bR)-8-(methoxymethoxy)-3a,5b-dimethyl-11,16-dioxo-2,3,3a,4,5,5a,5b,6,7,8,9,11,16,17b-tetradecahydro-1H-9a,17a-ethenobenzo[c]cyclopenta[h]phthalazino[2,3-a]cinnolin-3-yl)propanal
  参考文献：
  名称：

  Synthesis and evaluation of 4-deacetoxyagosterol A as an MDR-modulator

  摘要：

  4-Deacetoxyagosterol A was synthesized from ergosterol by utilizing reductive regioselective epoxy cleavage as a key reaction. This synthesized congener of agosterol A, a spongean MDR-modulator, showed similar MDR-modulating activity against KB CV-60 cells overexpressing MRP. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00502-3

文献信息

• Total Synthesis of Agosterol A: an MDR-Modulator from a Marine Sponge
  作者：Nobutoshi Murakami、Masanori Sugimoto、Mari Morita、Motomasa Kobayashi

  DOI：10.1002/1521-3765(20010618)7:12<2663::aid-chem26630>3.0.co;2-u

  日期：2001.6.18

  The first total synthesis of agosterol A, a modulator of multidrug resistance (MDR) mediated by P-gp and MRP1, and isolated from a marine sponge, was achieved from ergosterol by utilizing a regioselective epoxy-cleavage reaction and regioselective dehydroxylation as the key reactions.