5'-nitrospiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one | 133189-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5'-nitrospiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one
• 英文别名: 5'-nitrospiro[[1,3]dioxane-2,3'-indolin]-2'-one；5'-nitrospiro[1,3-dioxane-2,3'-1H-indole]-2'-one
• CAS: 133189-20-5
• 化学式: C₁₁H₁₀N₂O₅
• 分子量: 250.211
• InChiKey: WCEFWTXRXYPMEI-UHFFFAOYSA-N

物化性质

• 沸点：
  507.9±50.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-nitrospiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one 在 一水合肼 作用下， 以 甲醇 、 水 为溶剂， 以98%的产率得到5'-aminospiro[[1,3]dioxane-2,3'-indolin]-2'-one
  参考文献：
  名称：

  [EN] SUBSTITUTED OXINDOL CB2 AGONISTS FOR PAIN TREATMENT
  [FR] AGONISTES DE CB2 DE TYPE OXINDOLE SUBSTITUÉ POUR LE TRAITEMENT DE LA DOULEUR

  摘要：

  提供了3-取代吲哚衍生物，它们是CB2受体的激动剂，包含相同衍生物的药物组合物，以及使用这些3-取代吲哚衍生物和组合物治疗与CB2介导的疾病（例如疼痛、癌症等）相关的方法。

  公开号：

  WO2010077839A1
• 作为产物：
  描述：

  5-硝基靛红 、 1,3-丙二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 14.0h， 以96%的产率得到5'-nitrospiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one
  参考文献：
  名称：

  3,4-Dihydropyrimido(1,2-a)indol-10(2H)-ones as potent non-peptidic inhibitors of caspase-3

  摘要：

  Cysteine-dependant aspartyl protease (caspase) activation has been implicated as a part of the signal transduction pathway leading to apoptosis. It has been postulated that caspase-3 inhibition could attenuate cell damage after an ischemic event and thereby providing for a novel neuroprotective treatment for stroke. As part of a program to develop a small molecule inhibitor of caspase-3, a novel series of 3,4-dihydropyrimido(1,2-a)indol-10(2H)-ones (pyrimidoindolones) was identified. The synthesis, biological evaluation and structure-activity relationships of the pyrimidoindolones are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.036

文献信息

• Pyrimidoindolones and methods for using same
  申请人：Dollings Jeffrey Paul

  公开号：US20050250798A1

  公开（公告）日：2005-11-10

  Novel pyrimidoindolone compounds are disclosed. Methods of using the pyrimidoindolone compounds and compositions containing the compounds in the treatment and/or prevention of disease and other conditions related to inflammation, neurodegeneration, osteoarthritis and apoptosis are also disclosed.

  揭示了一种新型的嘧啶吲哚酮化合物。还揭示了使用这些嘧啶吲哚酮化合物的方法，以及包含这些化合物的组合物在治疗和/或预防与炎症、神经退行性疾病、骨关节炎和细胞凋亡相关的疾病和其他情况中的应用。
• [EN] SUBSTITUTED OXINDOLE CB2 AGONISTS<br/>[FR] AGONISTES DE CB2 DE TYPE OXINDOLE SUBSTITUÉ
  申请人：WYETH LLC

  公开号：WO2010090680A1

  公开（公告）日：2010-08-12

  Provided are substituted compounds, or pharmaceutically acceptable salts thereof, wherein: R1 is selected from -(CH2)nRa, -CH(OH)Ra, -CH(ORb)Ra, and -C(O)Ra, or is selected from ORa, SRa, SORa, SO2Ra and NRaRb; R2 and R3 are independently selected from H, halogen, OH, ORa, OWRa, C1-6 alkyl, and WC 1-6 alkyl, wherein C1-6 alkyl or ORa, is optionally substituted with 1, 2, or 3 substitutents independently selected from halogen, CN, OH, ORa, C1-6 alkyl, C1-6 haloalkyl, C3-8cycloalkyl, C6-10 aryl and C4-10 heteroaryl; or R2 and R3, together with the carbon atom to which they are attached, join to form a ring selected from 3-8 membered cycloalkyl, 3-8 membered heterocycloalkyl, C5-C7 oxycycloalkyl, C5.7 dioxycycloalkyl and oxazolidinyl ring, each ring optionally substituted with 1, 2, or 3 substituents independently selected from halogen, CN, OH, 0Ra, C1-6alkyl, C1-6 haloalkyl, C3-8 cycloalkyl, C6-10aryl and C4-10 heteroaryl; R4 is independently selected from H.C1-6 alkyl, C2-6 alkenyl, C2-6alkynyl, C6-10 aryl, C4-10 heteroaryl, -(CH2)n-benzodioxane, -(CH2)n- oxazolidinone and -(CH2)n-C1-6 haloalkyl, each of which is optionally substituted with 1, 2, or 3 substitutents independently selected from halogen, CN, OH, ORa, C1-6 alkyl, C1-6 haloalkyl, C3.8 cycloalkyl, WC3.8 cycloalkyl, C6-10 aryl and C4.10 heteroaryl; which are agonists of the CB2 receptor, pharmaceutical compositions containing the same, and methods of treatment related to CB2-mediated disorders (eg., pain, cancer etc.) using the substituted oxindole compounds and compositions described herein.

  提供的是替代化合物，或其药用盐，其中：R1从-(CH2)nRa，-CH(OH)Ra，-CH(ORb)Ra和-C(O)Ra中选择，或从ORa，SRa，SORa，SO2Ra和NRaRb中选择；R2和R3独立选择自H，卤素，OH，ORa，OWRa，C1-6烷基和WC 1-6烷基，其中C1-6烷基或ORa，可选地取代为1、2或3个取代基，独立选择自卤素，CN，OH，ORa，C1-6烷基，C1-6卤代烷基，C3-8环烷基，C6-10芳基和C4-10杂环芳基；或R2和R3，与它们连接的碳原子一起，结合形成选择自3-8环烷基，3-8杂环烷基，C5-C7氧杂环烷基，C5.7二氧杂环烷基和噁唑烷基的环，每个环可选地取代为1、2或3个取代基，独立选择自卤素，CN，OH，0Ra，C1-6烷基，C1-6卤代烷基，C3-8环烷基，C6-10芳基和C4-10杂环芳基；R4独立选择自H.C1-6烷基，C2-6烯基，C2-6炔基，C6-10芳基，C4-10杂环芳基，-(CH2)n-苯二氧杂环己，-(CH2)n-噁唑烷酮和-(CH2)n-C1-6卤代烷基，每种都可选地取代为1、2或3个取代基，独立选择自卤素，CN，OH，ORa，C1-6烷基，C1-6卤代烷基，C3.8环烷基，WC3.8环烷基，C6-10芳基和C4.10杂环芳基；这些化合物是CB2受体的激动剂，包含它们的药物组合物，以及使用所述的替代氧吲哚化合物和组合物治疗与CB2介导的疾病（例如疼痛、癌症等）相关的方法。
• PYRIMIDOINDOLONES AND METHODS FOR USING SAME
  申请人：Dollings Jeffrey Paul

  公开号：US20070270587A1

  公开（公告）日：2007-11-22

  Novel pyrimidoindolone compounds are disclosed. Methods of using the pyrimidoindolone compounds and compositions containing the compounds in the treatment and/or prevention of disease and other conditions related to inflammation, neurodegeneration, osteoarthritis and apoptosis are also disclosed.

  本发明揭示了新型嘧啶并吲哚酮类化合物。还揭示了使用这些嘧啶并吲哚酮类化合物和含有这些化合物的组合物在治疗和/或预防与炎症、神经退行性、骨关节炎和细胞凋亡等疾病和其他相关病症方面的方法。
• Synthesis of heteroaromatic N-β-glycosides of N-acetylglucosamine under phase transfer conditions: II. Indolin-2-one glycosaminides
  作者：V. O. Kur’yanov、T. A. Chupakhina、O. V. Shishkin、S. V. Shishkina、V. Ya. Chirva

  DOI：10.1134/s1068162008060137

  日期：2008.11

  Regioselective N-beta-glucosamination of various unsubstituted or C4-, C5-, or C6-monosubstituted indolin-2-ones under phase transfer conditions was studied. The regioselectivity was unambiguously proved by H-1 NMR spectroscopy and X-ray analysis. The presence of substituent at C7 of the aromatic ring leads to the formation of either a mixture of isomeric N-beta- and O-beta-D-glucosaminides, or only oxazoline and/or 2-acetamidoglycal irrespective of the reaction conditions.
• US7256198B2
  申请人：——

  公开号：US7256198B2

  公开（公告）日：2007-08-14