2-(4-chloromethyl-benzyl)-isoindole-1,3-dione | 61895-53-2

• 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-(4-chloromethyl-benzyl)-isoindole-1,3-dione
• 英文别名: 2-(4-chloromethylbenzyl)isoindole-1,3-dione；N-[4-(chlorometyl)benzyl]phthalimide；N-(4-chloromethyl-benzyl)-phthalimide；N-(4-Chlormethyl-benzyl)-phthalimid；α-phthalimido-α'-chloroxylene；4-Phthalimidomethylbenzylchlorid；2-{[4-(Chloromethyl)phenyl]methyl}-1H-isoindole-1,3(2H)-dione；2-[[4-(chloromethyl)phenyl]methyl]isoindole-1,3-dione
• CAS: 61895-53-2
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: PRLFXMNGWLYTHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  143-146 °C(Solv: acetone (67-64-1))
• 沸点：
  451.4±33.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chloromethyl-benzyl)-isoindole-1,3-dione 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 异丙醇 、 丙酮 为溶剂， 反应 48.5h， 生成 2-(3-{7-[4-(5-tert-butoxycarbonylmethoxy-naphthalen-1-yloxymethyl)-benzyl]-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl}-propionylamino)-succinic acid di-tert-butyl ester
  参考文献：
  名称：

  Synthesis and Conformational Characterization of Tethered, Self-Complexing 1,5-Dialkoxynaphthalene/1,4,5,8-Naphthalenetetracarboxylic Diimide Systems

  摘要：

  Chemists are beginning to explore the abiotic folding of synthetic chains, and the term "foldamers" has been used to characterize oligomers with a strong inclination to adopt specific, compact conformations. The characterization of folded structure in solution is one of the difficult challenges facing the foldamer Field. Aedamers were the first foldamers to make use of aromatic-aromatic interactions in water to direct folding and were designed to have several spectroscopic handles with which to probe folding conformations in solution. Herein is reported the synthesis and spectroscopic characterization of eleven aedamer dimers, with linkers chosen to provide a spectrum of lengths and flexibilities. The dimers, composed of one electron rich (1,5-dialkoxynaphthalene) and one electron deficient (1,4,5,8-naphthalenetetracarboxylic diimide) aromatic group tethered by a linker, are the smallest aedamer folding unit. The powerful spectroscopic handles associated with the stacked aedamer groups were exploited in a comprehensive spectroscopic analysis of conformation that included UV-vis absorption spectroscopy, fluorescence measurements (including time-resolved studies), as well as detailed NMR studies. The spectra were interpreted in the context of molecular modeling/spectral prediction and structural models were developed for the different dimers in aqueous solution. In most instances, the observed data was best described by an ensemble of predicted structures as opposed to one or few conformers. Thus, in the case of these aedamer dimers, "folding" does not appear to imply a two-state model with a rigid, unique conformation. Rather, the reported analysis indicates the data can best be described by a more dynamic model in which a given molecule spends its time in different folded conformations that are related by having a characteristic face-to-face stacking arrangement of the aromatic units.

  DOI：

  10.1021/ja0019225
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 乙醇 作用下， 生成 2-(4-chloromethyl-benzyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Funke et al., Annales de l'Institut Pasteur, 1946, vol. 72, p. 264,267

  摘要：

  DOI：

文献信息

• The Effect of Carboxamide/Sulfonamide Replacement in Arylpiperazinylalkyl Derivatives on Activity to Serotonin and Dopamine Receptors
  作者：Piotr Kowalski、Paweł Śliwa、Grzegorz Satała、Rafał Kurczab、Ilona Bartos、Karol Zuchowicz

  DOI：10.1002/ardp.201700090

  日期：2017.10

  both p‐xylyl and benzyl derivatives had the highest affinity for the dopamine D2 receptor (i.e., 16 out of 24 compounds investigated have an affinity below 100 nM). A molecular modeling study of carboxamide 9a and sulfonamide 9b showed that their binding effects to each of 5‐HT1AR and D2R created binding modes interaction with different conserved receptors residues. Structural similarities of carboxamide

  制备了一系列甲酰胺和磺酰胺烷基（对二甲苯基和苄基）1-（2-甲氧基苯基）哌嗪（o-OMe-PhP）和 1-（2,3-二氯苯基）哌嗪（2,3-DCPP）类似物并测试了它们与血清素 5-HT1A/5-HT6/5-HT7 和多巴胺 D2 受体结合的亲和力。这种化学修饰让我们探索用磺酰胺基团取代羧酰胺对亲和力变化的影响。在 o-OMe-PhP 和 2,3-DCPP 系列中，羧酰胺与磺酰胺对 5-HT1A/5-HT6/5-HT7 和 D2 受体的相对活性显示出相似的趋势。发现具有对二甲苯基间隔基的羧酰胺/磺酰胺对特定受体具有不同或相似的活性，而在检查的两类羧酰胺和磺酰胺中，磺胺类的苄基衍生物显示出最高的血清素能亲和力，特别是对 5-HT7 受体 (Ki 8-85 nM)。Ki 值表明，无论羧酰胺/磺酰胺区如何，对二甲苯基和苄基衍生物对多巴胺 D2 受体的亲和力最高（即，所研究的 24 种化合物中有 16
• New Arylpiperazines with Flexible versus Partly Constrained Linker as Serotonin 5-HT_1A/5-HT₇Receptor Ligands
  作者：Piotr Kowalski、Katarzyna Mitka、Jolanta Jaśkowska、Beata Duszyńska、Andrzej J. Bojarski

  DOI：10.1002/ardp.201300011

  日期：2013.5

  A series of new long‐chain arylpiperazine (LCAP) derivatives with flexible and partly constrained alkyl linker were synthesized and investigated in vitro as potential serotonin 5‐HT1A and 5‐HT7 receptor ligands. The compounds were prepared by a two‐step procedure using naphthalimide and 2H‐1,3‐benzoxazine‐2,4(3H)‐dione as imides, and 1‐(2‐methoxyphenyl)piperazine (o‐OMe‐PhP) and 1,2,3,4‐tetrahydroisoquinoline

  合成了一系列具有灵活且部分受限的烷基接头的新型长链芳基哌嗪 (LCAP) 衍生物，并在体外作为潜在的血清素 5-HT1A 和 5-HT7 受体配体进行了研究。使用萘二甲酰亚胺和 2H-1,3-苯并恶嗪-2,4(3H)-二酮作为酰亚胺，以及 1-(2-甲氧基苯基)哌嗪 (o-OMe-PhP) 和 1 ,2,3,4-四氢异喹啉 (THIQ) 作为胺药效团。间隔结构的修改包括引入灵活的五亚甲基和六亚甲基链以及部分受限的间和对二甲苯基部分。一般而言，新化合物对 5-HT1A 的活性高于对 5-HT7 受体的活性，并且 o-OMe-PhP 衍生物比其各自的 THIQ 类似物表现出更高的亲和力。间隔修饰对观察到的体外活性几乎没有影响。在 o-OMe-PhP 系列中，除了含有间二甲苯基部分的配体的结合略有减少外，化合物对两种受体的效力没有实质性变化，而对于 THIQ 衍生物，具有明确的构效关系仅在化合物与
• S-Adenosylmethionine decarboxylase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0351475A1

  公开（公告）日：1990-01-24

  This invention relates to novel chemical compounds useful as S-adenosylmethionine decarboxylase inhibitors, of the formula H₂N-Q--Al wherein Al represents 5'-deoxyadenosyl.      represents adenosinyl, R represents H, methyl or ethyl and Q represents moieties of formulae Ia to If depicted as follows: wherein R₁ is H or F, n is 1 or 2, V₁ is H or CH₃, V₂ is H or COOH, and each of W, X, Y, and Z are H, F, Cl or Br. To the processes useful for their preperation and to their use in the treatment of a variety of condition and disease states associated with a rapid proliferation of cell growth.

  这项发明涉及一种新型化合物，可用作S-腺苷甲硫氨酸脱羧酶抑制剂，其化学式为H₂N-Q--Al，其中Al代表5'-去氧腺苷基。     代表腺苷基，R代表H、甲基或乙基，Q代表如下所示的化学式Ia至If的基团：其中R₁为H或F，n为1或2，V₁为H或CH₃，V₂为H或COOH，而W、X、Y和Z中的每一个均为H、F、Cl或Br。还涉及用于其制备的方法以及它们在治疗与细胞增殖快速增加相关的各种疾病和病症中的应用。
• 5'-amine substituted adenosine analogs as immunosuppressants
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05308837A1

  公开（公告）日：1994-05-03

  The present invention relates to a method of effecting immunosuppression in a patient in need thereof comprising administering to said patient an effective immunosuppressive amount of certain 5'-amine substituted adenosine analogs.

  本发明涉及一种在需要免疫抑制的患者中实现免疫抑制的方法，包括向该患者施用一定量的特定5'-氨基取代腺苷类似物。
• S-adenosyl methionine decarboxylase inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05416076A1

  公开（公告）日：1995-05-16

  The adenosine derivatives represented by the following formula: ##STR1## and the pharmaceutically acceptable salts thereof wherein R is H or C.sub.1 -C.sub.7 alkyl, Q is the moiety of the formula ##STR2## wherein V is H or --COOH X is H, F, Cl, Br, and Z is H, F, Cl, or Br. These compounds are inhibitors of S-adenosylmethione decarboxylase and are useful for treating parasitic infections.

  以下公式代表的腺苷衍生物：其中R为H或C.sub.1 -C.sub.7烷基，Q为以下公式的基团：其中V为H或--COOH，X为H，F，Cl，Br，Z为H，F，Cl或Br。这些化合物是S-腺苷甲硫氨酸脱羧酶的抑制剂，可用于治疗寄生虫感染。