(1,7,8-Trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl) butanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1,7,8-Trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl) butanoate
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.3
• InChiKey: HTJGLYIJVSDQAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  90.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  栗精胺 、 丁酰氯 、 水 、 二氯甲烷 在 ice 作用下， 以 吡啶 、 氯仿 、 甲醇 为溶剂， 反应 72.0h， 以to provide 68 mg of [1S-(lα, 6β, 7α, 8β, 8αβ) ]-octahydro-1,6,7,8-indolizinetetrol 6-butanoate的产率得到(1,7,8-Trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl) butanoate
  参考文献：
  名称：

  Castanospermine esters and glycosides

  摘要：

  本文描述了作为碳水化合物消化酶抑制剂并用于治疗糖尿病的Castanospermine单酯、双酯和糖苷。该化合物是通过将Castanospermine与适当的酸卤或酸酐或适当的糖基卤或糖基乙酰亚胺反应而制备的，反应条件有利于分离单酯化、双酯化和糖基化产物。还可以使用各种可在温和条件下选择性去除的阻断基来促进某些异构体的形成。

  公开号：

  US05017563A1

文献信息

• Anti-herpes castanospermine esters
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05385911A1

  公开（公告）日：1995-01-31

  Certain Castanospermine ester derivatives of the formula: ##STR1## wherein R, R.sub.1 and R.sub.2 are each independently hydrogen, C.sub.1-14 alkanoyl, C.sub.1-14 alkenoyl, cyclohexanecarbonyl, C.sub.1-8 alkoxyacetyl, ##STR2## naphthalenecarbonyl optionally substituted by methyl or halogen; phenyl (C.sub.2-6 alkanoyl) wherein the phenyl is optionally substituted by methyl or halogen; cinnamoyl; pyridinecarbonyl optionally substituted by methyl or halogen; dihydropyridine carbonyl optionally substituted by C.sub.1 -C.sub.10 alkyl; thiophenecarbonyl optionally substituted by methyl or halogen; or furancarbonyl optionally substituted by methyl or halogen; Y is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen, trifluoromethyl, C.sub.1-4 alkylsulfonyl, C.sub.1-4 alkylmercapto, cyano or dimethylamino; Y' is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or it is combined with Y to give 3,4-methylenedioxy; Y" is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halogen; with R, R.sub.1 and R.sub.2 being selected in such a way that at least one of them, but not more than two of them, is hydrogen; are disclosed to be effective in treating diseases caused by Herpes Simplex Virus (HSV) Types 1 and 2.

  本发明涉及一种公式如下的某些Castanospermine酯衍生物：##STR1##其中，R、R.sub.1和R.sub.2各自独立地为氢、C.sub.1-14烷酰基、C.sub.1-14烯酰基、环己基羰基、C.sub.1-8烷氧基乙酰基、##STR2##萘基羰基，选择性地被甲基或卤素取代；苯基（C.sub.2-6烷酰基），其中苯基被甲基或卤素选择性地取代；肉桂酰基；吡啶基羰基，选择性地被甲基或卤素取代；二氢吡啶羰基，选择性地被C.sub.1-C.sub.10烷基取代；噻吩羰基，选择性地被甲基或卤素取代；或呋喃羰基，选择性地被甲基或卤素取代；Y为氢、C.sub.1-4烷基、C.sub.1-4烷氧基、卤素、三氟甲基、C.sub.1-4烷基磺酰基、C.sub.1-4烷基硫醇基、氰基或二甲基氨基；Y'为氢、C.sub.1-4烷基、C.sub.1-4烷氧基、卤素或与Y组合形成3,4-亚甲二氧基；Y"为氢、C.sub.1-4烷基、C.sub.1-4烷氧基或卤素；其中，R、R.sub.1和R.sub.2的选择方式使它们中至少有一个，但不超过两个，为氢。本发明揭示了这些化合物在治疗由单纯疱疹病毒（HSV）1型和2型引起的疾病方面的有效性。
• Castanospermine esters in the inhibition of tumor metastasis
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0373663A2

  公开（公告）日：1990-06-20

  A method for the inhibition of tumor metastases is described herein. The method makes use of the administra­tion of certain castanospermine esters or their pharma­ceutically acceptable salts.

  本文描述了一种抑制肿瘤转移的方法。该方法利用了某些蓖麻籽酯类或其药学上可接受的盐类。
• COMPOSITIONS AND METHODS FOR TREATING OR PREVENTING HEPADNAVIRIDAE INFECTION
  申请人：MIGENIX INC.

  公开号：EP1789043A2

  公开（公告）日：2007-05-30
• COMPOUNDS FOR THE TREATMENT OF FLAVIVIRAL INFECTIONS
  申请人：De Moor Olivier

  公开号：US20110195929A1

  公开（公告）日：2011-08-11

  Described are various compounds and methods for the treatment of flaviviral infections. In particular, alkaloids and imino sugars in arabinose and/or lyxose stereochemical configuration with antiflaviviral activity are described.
• TREATMENT OF LYSOSOMAL STORAGE DISORDERS AND OTHER PROTEOSTATIC DISEASES
  申请人：De Moor Olivier

  公开号：US20110237538A1

  公开（公告）日：2011-09-29

  Described are various compounds, in particular iminosugars, and methods for the treatment of proteostatic diseases, in particular lysosomal storage disorders. The compound may be a pharmacoperone of an enzyme selected from: (a) Acid alpha-glucosidase; (b) Acid beta-glucosidase; (c) glucocerebrosidase; (d) alpha-Galactosidase A; (e) Acid beta-galactosidase; (f) beta-Hexosaminidase A; (g) beta-Hexosaminidase B; (h) Acid sphingomyelinase; (i) Galactocerebrosidase; (j) Acid ceramidase; (k) Arylsulfatase A; (l) alpha-L-Iduronidase; (m) Iduronate-2-sulfatase; (n) Heparan N-sulfatase; (o) alpha-N-Acetylglucosaminidase; (p) Acetyl-CoA: alpha-glucosaminide N-acetyltransferase; (q) N-Acetylglucosamine-6-sulfate sulfatase; (r) N-Acetylgalactosamine-6-sulfate sulfatase; (s) Acid beta-galactosidase; (t) Arylsulfatase B; (u) beta-Glucuronidase; (v) Acid alpha-mannosidase; (w) Acid beta-mannosidase; (x) Acid alpha-L-fucosidase; (y) Sialidase; and (z) alpha-N-acetylgalactosaminidase.