2-(4-methyl-2-pyridinyl)-1H-isoindole-1,3(2H)-dione | 106204-03-9

• 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-methyl-2-pyridinyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-(4-methylpyridin-2-yl)isoindoline-1,3-dione；2-(N-phthalimido)-4-picoline；4-methyl-2-phthalimidopyridine；N-(4-methyl-pyridin-2-yl)-phthalimide；2-(4-methyl-pyridin-2-yl)-isoindole-1,3-dione；4-Methyl-2-phthalimidyl-pyridin；2-(4-methylpyridin-2-yl)isoindole-1,3-dione
• CAS: 106204-03-9
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: DNJNBNSEZWBVOR-UHFFFAOYSA-N

物化性质

• 沸点：
  451.4±47.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)
• 溶解度：
  >35.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methyl-2-pyridinyl)-1H-isoindole-1,3(2H)-dione 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 吡啶 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成 [1-[(2-aminopyridin-4-yl)methyl]piperidin-4-yl]-[4-[C-(3,5-dichlorophenyl)-N-methoxycarbonimidoyl]piperidin-1-yl]methanone
  参考文献：
  名称：

  WO2008/108957

  摘要：

  公开号：
• 作为产物：
  描述：

  邻苯二甲酸单甲酯 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2-(4-methyl-2-pyridinyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors

  摘要：

  This paper describes the synthesis of N-pyridinyl(alkyl)phthalimides related to N-phenyl-4,5,6,7-tetrafluorophthalimides known to be inhibitors of tumour necrosis factor-alpha (TNF alpha) production. Pharmacomodulation at the phthalimidic nitrogen led to the selection of two pharmacophoric fragments (2,4-lutidinyl and beta -picolyl), allowing significant inhibition of TNF alpha production (compounds 12 and 17). Variation of the substituents linked to the homocycle of their phthalimide scaffold indicated that high (TNF alpha production) inhibitory potency could be achieved, notably by 5-fluoro, 4- or 5-nitro, 5-amino and especially tetrafluoro substitution. The most active compound, N-(pyridin-3-ylmethyl)-4,5,6,7-tetrafluorophthalimide (32) (84% inhibition at 10 muM), also produced an anti-oedematous effect in the PMA-induced mouse-ear swelling test. Although less active than dexamethasone, it exerted a marked reduction in ear thickness after oral administration (63% vs. 85% for dexamethasone at 0.2 mM kg(-1)) and remained efficient after topical application (46% vs. 96% for the dexamethasone). It also induced potent inhibition in the rat carrageenan foot oedema test with an ID50 (0.14 muM kg(-1)) comparable with that of N-(2,6-diisopropylphenyl)phthalimide (4) (0.15 muM kg(-1)). (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01254-5

文献信息

• [EN] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES AS HISTAMINE H3 ANTAGONISTS<br/>[FR] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR H3 DE L'HISTAMINE
  申请人：SCHERING CORP

  公开号：WO2003103669A1

  公开（公告）日：2003-12-18

  Disclosed are histamine H3 antagonists of the formula (I) wherein R1 is benzimidazolone derivative, M1 and M2 are optionally substituted carbon or nitrogen, R2 includes optionally substituted aryl or heteroaryl, and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of Formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of formula (I) in combination with a H1 receptor antagonist.

  揭示了公式（I）中的组胺H3拮抗剂，其中R1是苯并咪唑酮衍生物，M1和M2是可选择地取代的碳或氮，R2包括可选择地取代的芳基或杂环基，其余变量如规范中所定义。还揭示了包括公式（I）化合物的药物组合物。还揭示了使用公式（I）化合物治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）的方法。还揭示了使用公式（I）化合物与H1受体拮抗剂结合治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）。
• Novel HIV reverse transcriptase inhibitors
  申请人：Guo Hongyan

  公开号：US20080070920A1

  公开（公告）日：2008-03-20

  The invention is related to compounds of Formula (I), (II), or (III): or a pharmaceutically acceptable salt, solvate, ester, and/or phosphonate thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.

  这项发明涉及到以下化合物的公式(I)、(II)或(III)： 或其药用可接受的盐、溶剂化合物、酯和/或膦酸酯，含有这种化合物的组合物，以及包括给予这种化合物的治疗方法。
• Antithrombotic agents
  申请人：Eli Lilly and Company

  公开号：US05914319A1

  公开（公告）日：1999-06-22

  This invention relates to thrombin inhibiting compounds having the Formula I X--Y--NH--(CH.sub.2).sub.r --G I where X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.

  这项发明涉及具有Formula I X--Y--NH--(CH.sub.2).sub.r --G I的抑制凝血酶化合物，其中X、Y、r和G的值在描述中有定义，以及含有这些化合物的药物配方和它们作为凝血酶抑制剂、凝血抑制剂和血栓性疾病药物的使用方法。
• Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide
  作者：Jianbin Chen、Kishore Natte、Anke Spannenberg、Helfried Neumann、Matthias Beller、Xiao-Feng Wu

  DOI：10.1039/c4ob00796d

  日期：——

  procedure for double carbonylation of o-dibromobenzenes with various 2-amino pyridines and naturally occurring amines, thus providing in good to excellent yields N-substituted phthalimides by using this palladium-catalyzed carbonylation procedure. Furthermore, for the first time we have applied the developed synthetic protocol for the synthesis of biologically active molecule thalidomide via a single step

  我们在此描述了一种方便且温和的程序，用于将邻二溴苯与各种2-氨基吡啶和天然存在的胺进行双羰基化，从而通过使用这种钯催化的羰基化程序，以良好至极好的收率提供N-取代的邻苯二甲酰亚胺。此外，我们首次将开发出的合成方案用于通过单步羰基化环化反应以优异的产率合成生物活性分子沙利度胺。
• 2-amino-4-trichloromethylpyridine and its preparation
  申请人：BASF Aktiengesellschaft

  公开号：US04699983A1

  公开（公告）日：1987-10-13

  2-Amino-4-trichloromethylpyridine of the formula I ##STR1## The compound is an effective nitrification inhibitor.

  化合物的名称为I式2-氨基-4-三氯甲基吡啶，公式为##STR1##。该化合物是一种有效的硝化抑制剂。