(-)-(3S,11bS)-3-amino-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one | 651032-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (-)-(3S,11bS)-3-amino-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one
• 英文别名: (3S,11bS)-3-amino-9,11-dihydroxy-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one
• CAS: 651032-70-1
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: MMDKSJRBOBOIRL-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  86.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(3S,11bS)-3-amino-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2'R)-N-((3S,11bS)-9,11-dihydroxy-2,3,4,6,7,11b-hexahydro-4-oxo-1H-pyrido[2,1-a]isoquinolin-3-yl)-3',3',3'-trifluoro-2'-methoxy-2'-phenylpropanamide
  参考文献：
  名称：

  Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei¹

  摘要：

  Three new alpha-glucosidase inhibitors, schulzeines A-C (1-3), were isolated from the marine sponge Penares schulzei. Their structures were elucidated by spectral analysis and chemical degradations to be the isoquinoline alkaloids, encompassing two amino acids, and C-28 fatty acid, the last of which was sulfated. Absolute stereochemistry of schulzeines was determined by application of the modified Mosher analysis to fragments obtained by chemical degradation. Schulzeines A-C inhibit alpha-glucosidase with IC50 values of 48-170 nM.

  DOI：

  10.1021/ja037368r
• 作为产物：
  描述：

  在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以91%的产率得到(-)-(3S,11bS)-3-amino-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one
  参考文献：
  名称：

  Formal Enantioselective Total Synthesis of Schulzeines A–C via Pd–Catalyzed Intramolecular Asymmetric Allylic Amination

  摘要：

  Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.

  DOI：

  10.1021/jo2009615

文献信息

• Formal synthesis of schulzeines B and C
  作者：Punlop Kuntiyong、Sunisa Akkarasamiyo、Nuanpan Piboonsrinakara、Chitlada Hemmara、Poramate Songthammawat

  DOI：10.1016/j.tet.2011.07.085

  日期：2011.10

  A formal synthesis of schulzeines B and C, marine natural products with inhibitory effect against α-glucosidase, has been achieved. The key reactions of the synthesis are N-acyliminium ion cyclization, Sharpless asymmetric dihydroxylation, olefin cross metathesis, and asymmetric allylboration.

  已经完成了具有舒张作用的B和C的合成，这是一种对α-葡萄糖苷酶具有抑制作用的海洋天然产物。合成的关键反应是N-酰基亚胺离子环化，Sharpless不对称二羟基化，烯烃交叉复分解和不对称烯丙基硼化。
• Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde
  作者：Gang Liu、Daniel Romo

  DOI：10.1021/ol802992m

  日期：2009.3.5

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.
• Formal Enantioselective Total Synthesis of Schulzeines A–C via Pd–Catalyzed Intramolecular Asymmetric Allylic Amination
  作者：Chi-Feng Lin、Iwao Ojima

  DOI：10.1021/jo2009615

  日期：2011.8.5

  Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.
• Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge <i>Penares schulzei</i>¹
  作者：Kentaro Takada、Taisuke Uehara、Yoichi Nakao、Shigeki Matsunaga、Rob W. M. van Soest、Nobuhiro Fusetani

  DOI：10.1021/ja037368r

  日期：2004.1.1

  Three new alpha-glucosidase inhibitors, schulzeines A-C (1-3), were isolated from the marine sponge Penares schulzei. Their structures were elucidated by spectral analysis and chemical degradations to be the isoquinoline alkaloids, encompassing two amino acids, and C-28 fatty acid, the last of which was sulfated. Absolute stereochemistry of schulzeines was determined by application of the modified Mosher analysis to fragments obtained by chemical degradation. Schulzeines A-C inhibit alpha-glucosidase with IC50 values of 48-170 nM.