2-(3-azido-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione | 200483-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(3-azido-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-(3-azido-2-hydroxypropyl)isoindoline-1,3-dione；N-(3-Azido-2-hydroxypropyl)phthalimide；2-(3-azido-2-hydroxypropyl)isoindole-1,3-dione
• CAS: 200483-38-1
• 化学式: C₁₁H₁₀N₄O₃
• 分子量: 246.225
• InChiKey: ZNFOYEMIXRVQNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-azido-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 2-[(2-oxo-5-oxazolidinyl)-methyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Madhusudhan; Ready, G. Om; Ramanatham, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 5, p. 1264 - 1268

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2,3-环氧丙基)邻苯二甲酰胺 在 sodium azide 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 以 水 为溶剂， 反应 0.5h， 以61%的产率得到2-(3-azido-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  在超声波/微波同时照射下，亲核试剂在水中有效区域选择性打开环氧化物

  摘要：

  在水性介质中亲核试剂对环氧化物的裂解可能会受到水本身的竞争，产生作为副产物的二醇。然而，当反应在高强度超声波或微波下进行时，亲核试剂的攻击被强烈促进，水不再反应。在同时超声/微波照射下取得了最好的结果：一系列单、二和三取代的环氧乙烷与叠氮化钠或 1-(3-氯苯基)哌嗪快速反应，通常会产生相应的更多取代的醇，收率可以接受到高收率. 这种无催化剂、更环保的方案以高区域选择性实现了环氧化物的更快裂解。

  DOI：

  10.1055/s-2007-984891

文献信息

• Novel amide derivatives as growth hormone secretagogues
  申请人：Ishiyama Nobuo

  公开号：US20060014701A1

  公开（公告）日：2006-01-19

  Disclosed are the novel compounds as growth hormone secretagogues represented by the structural Formula I: wherein R 1 is, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted amino, X is —CO— or —SO 2 —, Y is: wherein n is an integer from 0-4, R 4 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, R 5 and R 6 are independently selected from hydrogen, substituted or unsubstituted alkyl, or R 5 and R 6 or R 4 and R 5 are taken together to form substituted or unsubstituted alkylene, R 2 is hydrogen, or substituted or unsubstituted alkyl, R 3 is substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, D is substituted or unsubstituted amino, substituted or unsubstituted alkoxy, or substituted or unsubstituted alkylthio, * represents an asymmetric center, and pharmaceutically acceptable salts and individual isomers thereof, which have growth hormone releasing activity in humans or animals.

  本发明揭示了一种作为生长激素分泌素的新化合物，其结构式为I：其中R1是取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、或取代或未取代的氨基，X为—CO—或—SO2—，Y为：其中n为0-4的整数，R4为氢、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基，R5和R6独立地选自氢、取代或未取代的烷基，或R5和R6或R4和R5一起形成取代或未取代的烷基烯，R2为氢或取代或未取代的烷基，R3为取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基，D为取代或未取代的氨基、取代或未取代的烷氧基，或取代或未取代的烷硫基，*代表一个不对称中心，以及在人类或动物体内具有生长激素释放活性的药用可接受的盐和各个异构体。
• Amide derivatives as growth hormone secretagogues
  申请人：Kaken Pharmaceutical Co., Ltd.

  公开号：US07022677B1

  公开（公告）日：2006-04-04

  Disclosed are the novel compounds as growth hormone secretagogues represented by structural Formula (I), wherein R1 is, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted amino, X is —CO— or —SO2—, Y is Formula (II), wherein n is an integer from 0–4, R4 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, R5 and R6 are independently selected from hydrogen, substituted or unsubstituted alkyl, or R5 and R6 or R4 and R5 are taken together to form substituted or unsubstituted alkylene, R2 is hydrogen, or substituted or unsubstituted alkyl, R3 is substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, D is substituted or unsubstituted amino, substituted or unsubstituted alkoxy, or substituted or unsubstituted alkylthio, * represents an asymmetric center, and pharmaceutically acceptable salts and individual isomers thereof, which have growth hormone releasing activity in humans or animals.

  本发明涉及一种新型化合物，作为生长激素分泌素，其结构式表示为（I），其中R1是取代或未取代的烷基，取代或未取代的环烷基，取代或未取代的烷氧基，取代或未取代的芳基，或取代或未取代的氨基，X是—CO—或—SO2—，Y是式（II），其中n是0-4的整数，R4是氢，取代或未取代的烷基，取代或未取代的环烷基，取代或未取代的芳基，R5和R6独立选择自氢，取代或未取代的烷基，或R5和R6或R4和R5一起形成取代或未取代的亚烷基，R2是氢，或取代或未取代的烷基，R3是取代或未取代的烷基，取代或未取代的环烷基，取代或未取代的芳基，D是取代或未取代的氨基，取代或未取代的烷氧基，或取代或未取代的烷硫基，*表示不对称中心，以及其药学上可接受的盐和单一异构体，在人或动物中具有生长激素释放活性。
• Madhusudhan; Reddy, M. Srinivasa; Reddy, Y. Narayana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 7, p. 978 - 984
  作者：Madhusudhan、Reddy, M. Srinivasa、Reddy, Y. Narayana、Vijayalakshmi、Suribabu、Balraju

  DOI：——

  日期：——
• A straightforward and general access to α-phthalimido-α′-substituted propan-2-ones
  作者：Vittorio Pace、Wolfgang Holzer

  DOI：10.1016/j.tetlet.2012.07.045

  日期：2012.9

  The regioselective ring opening of the commercially available N-(2,3-epoxypropyl)phthalimide with different nucleophiles, to obtain the corresponding phthalimidopropan-2-ols (including a challenging fluorohydrin) followed by the Dess-Martin periodinane oxidation, constitutes a general and widely applicable protocol for the preparation of differently functionalized alpha-phthalimido-alpha'-substituted propan-2-ones. The incorporation of the substituent in the alpha' position takes place in an early stage of the process, thus furnishing a divergent and valuable approach. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel Series of Highly Potent Non-peptide Growth Hormone Secretagogues with Im- proved Bioavailability
  作者：Hirohide Ishige、Nobuo Ishiyama、Mitsuo Mimura、Mitsuo Hayashida、Tadashi Okuno、Kiyoharu Ukai、Takeshi Kiyofuji、Yasuo Yoneda、Shinji Tauchi、Akinori Aoyama、Kiyoshi Inoguchi

  DOI：10.3987/com-05-s(t)73

  日期：——

  The discovery and the SAR of acylproline derivatives as highly potent growth hormone secretagogues (GHSs) with good oral bioavailability are described. One representative compound, N-[3-(2,2-dimethylpropylamino)-2hydroxypropyl]-2(R)-[ 1-(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]3-naphthalen-2-ylpropionamide (4e), showed potent GHS activity (ED50=1 nM) and good oral bioavailability (BA=33.2%). Moreover, the optically pure N-[3-(2,2-dimethylpropylamino)-2(S)-hydroxypropyl]-2(R)-[ I -(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2-ylpropionamide ((2S)-4c) showed a good metabolic stability against in vitro clearance (human liver microsome) with potent GHS activity.