2-(4-溴丁基)-5-硝基-1H-异吲哚-1,3(2H-)-二酮 | 125207-39-8

• 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
• 中文名称: 2-(4-溴丁基)-5-硝基-1H-异吲哚-1,3(2H-)-二酮
• 英文名称: 2-(4-Bromobutyl)-5-nitro-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-(4-bromobutyl)-5-nitroisoindole-1,3-dione
• CAS: 125207-39-8
• 化学式: C₁₂H₁₁BrN₂O₄
• mdl: MFCD01313849
• 分子量: 327.134
• InChiKey: MQBKILMXULFSRI-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  2-(4-溴丁基)-5-硝基-1H-异吲哚-1,3(2H-)-二酮 在 盐酸 、 tin(II) chloride dihydrate 、 碳酸氢钠 、 potassium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Synthesis and Characterisation of 4-Aminophthalimido-N-Alkyl-Calix[4]Azacrown Derivatives

  摘要：

  通过还原 4-硝基-N-溴烷基邻苯二甲酰亚胺和 SnCl2 制备了两种 4-氨基-N-溴烷基邻苯二甲酰亚胺衍生物，并与钙[4]氮杂卓反应，得到了两种新的 4-氨基邻苯二甲酰亚胺-N-烷基-钙[4]氮杂卓衍生物。通过红外光谱、1H NMR、13C NMR 和 HRMS 对这些衍生物进行了表征，结果表明它们呈锥形构象，4-氨基邻苯二甲酰亚胺-N-烷基-钙[4]氮杂冠可能为 Cu2+ 提供一种潜在的荧光探针。

  DOI：

  10.3184/174751912x13320759388888
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 硫酸 、 硝酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成 2-(4-溴丁基)-5-硝基-1H-异吲哚-1,3(2H-)-二酮
  参考文献：
  名称：

  A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors

  摘要：

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.011

文献信息

• Central Cholinergic Agents. I. Potent Acethlcholinesterase Inhibitors, 2-(.OMEGA.-(N-Alkyl-N-(.OMEGA.-phenyl-alkyl)amino)alkyl)-1H-isoindole-1,3(2H)-diones, Based on a New Hypothesis of the Enzyme's Active Site.
  作者：Yuji ISHIHARA、Koki KATO、Giichi GOTO

  DOI：10.1248/cpb.39.3225

  日期：——

  It has been suggested that the active site of acetylcholinesterase contains a hydrophobic binding site (HBS-1), which is closely adjacent to both the anionic and the esteratic sites. In this paper, we assumed that there exists another hydrophobic binding site (HBS-2), some distance removed from the anionic site. On this assumption, a new working hypothesis was proposed for the design of acetylcholinesterase inhibitors. A series of 2-[ω-[N-alkyl-N-(ω-phenyl-alkyl)amino]alkyl]-1H-isoindole-1, 3(2H)-diones was designed based on this hypothesis and tested for its inhibitory activities on acetylcholinesterase. Some in this series were revealed to be more potent than physostigmine. Optimum activity was found to be associated with a five carbon chain length separating the benzylamino group from the 1H-isoindole-1, 3(2H)-dione (phthalimide) moiety. Quantitative study of substitution effect on the phthalimide moiety revealed that hydrophilic and electron-withdrawing groups enhance the activity.

  有人提出，乙酰胆碱酯酶的活性部位包含一个疏水性结合位点(HBS-1)，该位点紧邻阴离子位点和酯酶位点。本文假设存在另一个疏水性结合位点(HBS-2)，该位点与阴离子位点相距一定距离。基于此假设，我们提出了设计新型乙酰胆碱酯酶抑制剂的工作假说。依据该假说，设计了一系列2-[ω-[N-烷基-N-(ω-苯基-烷基)氨基]烷基]-1H-异吲哚-1,3(2H)-二酮，并测试了它们对乙酰胆碱酯酶的抑制活性。系列中某些化合物的抑制活性显示出比毒扁豆碱更强的效力。最佳活性与苄氨基与1H-异吲哚-1,3(2H)-二酮(邻苯二甲酰亚胺)部分之间间隔五个碳原子相关。对邻苯二甲酰亚胺部分进行取代效应的定量研究发现，亲水性和吸电子基团能提高活性。
• Alkylene diamines
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05025033A1

  公开（公告）日：1991-06-18

  A cholinesterase inhibiting agent which contains an alkylene diamine of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently is a hydrogen atom or a hydrocarbon residue which may optionally be substituted, or R.sup.1 and R.sup.2 combinedly form, together with the adjacent nitrogen atom, a condensed heterocyclic group, R.sup.3 is a hydrogen atom or a hydrocarbon residue or an acyl group which may optionally be substituted and R.sup.4 is a hydrogen atom, or R.sup.3 and R.sup.4 combinedly form a group of the formula ##STR2## or --(CH.sub.2).sub.m+1 -- (m being 0, 1 or 2), A is --(CH.sub.2).sub.l -- (l being 0, 1 or 2) or --CH.dbd.CH--, X is a substituent or substituents and n is an integer of 4 to 7, or a salt thereof, which are useful as cerebral function improving agents for the prevention or treatment of senile dementia, Alzheimer's disease, Huntington's chorea, hyperkinesia, mania and so forth.

  一种抑制胆碱酯酶的药物，含有式为##STR1##的烷基二胺，其中R.sup.1和R.sup.2各自独立地是氢原子或一个可以选择性地被取代的烃基残基，或者R.sup.1和R.sup.2与相邻的氮原子一起形成一个紧凑的杂环基团，R.sup.3是氢原子或一个可以选择性地被取代的烃基残基或酰基，R.sup.4是氢原子，或者R.sup.3和R.sup.4组合形成式为##STR2##或--(CH.sub.2).sub.m+1 --（其中m为0、1或2），A是--(CH.sub.2).sub.l --（其中l为0、1或2）或--CH.dbd.CH--，X是取代基或取代基，n为4至7的整数，或其盐，这些药物可用作预防或治疗老年性痴呆、阿尔茨海默病、亨廷顿舞蹈症、多动症、狂躁等脑功能改善剂。
• Intramolecular Complex Formation between Flexible Molecular Tweezers and Weak Electron Acceptor
  作者：Yoshimasa Fukazawa、Hirotaka Kurebayashi

  DOI：10.3987/com-00-s(i)81

  日期：——
• NEW J. S.; YEVICH J. P.; EISON M. S.; TAYLOR D. P.; EISON A. S.; RIBLET L+, J. MED. CHEM., 29,(1986) N 8, 1476-1482
  作者：NEW J. S.、 YEVICH J. P.、 EISON M. S.、 TAYLOR D. P.、 EISON A. S.、 RIBLET L+

  DOI：——

  日期：——
• US5025033A
  申请人：——

  公开号：US5025033A

  公开（公告）日：1991-06-18