7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione | 252894-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione
• 英文别名: 7-iodo-3,4-dihydro-1H-benzazepine-2,5-dione；7-iodo-1H-[1]benzazepine-2,5-(3H,4H)-dione；7-iodo-3,4-dihydro-1H-benzo[b]azepine-2,5-dione；7-iodo-1H-[1]benzazepin-2,5-(3H, 4H)-dione；7-iodo-1H-[1]benzazepine-2,5(3H,4H)-dione
• CAS: 252894-39-6
• 化学式: C₁₀H₈INO₂
• 分子量: 301.084
• InChiKey: ZNPKGRMEAGEQIR-UHFFFAOYSA-N

物化性质

• 沸点：
  463.8±45.0 °C(Predicted)
• 密度：
  1.823±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione 在 palladium diacetate 、 TEA 、 溶剂黄146 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-(6-oxo-9-trifluoromethyl-5,6,7,12-tetrahydro-indolo[3,2-d][1]benzazepin-2-yl)-acrylonitrile
  参考文献：
  名称：

  2-Substituted paullones: CDK1/cyclin B-inhibiting property and in vitro antiproliferative activity

  摘要：

  9-Trifluoromethyl-paullones with a carbon chain in the 2-position were synthesized by palladium-catalyzed coupling reactions of a 2-iodoprecursor with terminal alkenes or alkynes, respectively. The introduction of a 2-cyanoethyl substituent led to a significant enhancement of CDK1/cyclin B inhibiting property and in vitro antiproliferative activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00048-2
• 作为产物：
  描述：

  2-氨基-5-碘苯甲酸乙酯 在 吡啶 、 potassium hydride 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione
  参考文献：
  名称：

  2-Substituted paullones: CDK1/cyclin B-inhibiting property and in vitro antiproliferative activity

  摘要：

  9-Trifluoromethyl-paullones with a carbon chain in the 2-position were synthesized by palladium-catalyzed coupling reactions of a 2-iodoprecursor with terminal alkenes or alkynes, respectively. The introduction of a 2-cyanoethyl substituent led to a significant enhancement of CDK1/cyclin B inhibiting property and in vitro antiproliferative activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00048-2

文献信息

• Synthesis and Structure of Fluorescent Chelate Boron Complexes of 4-Anilinomethylidene-1-benzazepine-2,5-dione Ligands
  作者：Conrad Kunick、Nadine Tolle、Ute Dunkel、Luciano Oehninger、Ingo Ott、Lutz Preu、Tobias Haase、Soenke Behrends、Peter Jones、Frank Totzke、Christoph Schächtele、Michael Kubbutat

  DOI：10.1055/s-0030-1260165

  日期：2011.9

  As analogues to the paullone kinase inhibitor family, boron chelate complexes of 4-anilinomethylidene-1-benzazepine-2,5-diones were prepared by reacting the ligands with boron trifluoride etherate or triphenylborane. The structures of the novel heterocyclic ring systems were established by X-ray structure analysis of two representative derivatives. The stability of the compounds in dimethylsulfoxide solution is dependent on the electronic properties of the aryl ring substituents. The fluorescent properties of the molecules are suitable for imaging the intracellular compound distribution by confocal laser microscopy.

  作为paullone激酶抑制剂家族的类似物，4-苯胺亚甲基-1-苯并氮杂卓-2,5-二酮的硼配位复合物是通过配体与三氟化硼乙醷或三苯基硼反应制备的。通过两个代表性衍生物的X射线结构分析确定了新型杂环体系的结构。这些化合物在二甲基亚砜溶液中的稳定性取决于芳环取代基的电子特性。这些分子的荧光特性适合于通过共聚焦激光显微镜成像细胞内化合物的分布。
• Fused azepinone cyclin dependent kinase inhibitors
  申请人：——

  公开号：US20020042412A1

  公开（公告）日：2002-04-11

  A new class of cyclin dependent kinase inhibitors that also have antiproliferative activity in human tumor cell line assays are described. Most of these compounds satisfy the formula 1 wherein A is oxygen or sulfur coupled to the right by a single or double bond; R 2 is selected from the group consisting of hydrogen, aryl, lower aliphatic substituents, particularly alkyl and lower alkyl ester; R 4 -R 7 are independently selected from the group consisting of alkoxy, amino, acyl, aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, aliphatic alcohols, particularly alkyl alcohols, aliphatic nitriles, particularly alkyl nitriles, cyano, nitro, carboxyl, halogen, hydrogen, hydroxyl, imino, and &agr;, &bgr;, unsaturated ketones; R 8 -R 11 are independently selected from the group consisting of aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, particularly lower aliphatic substituents, alipahatic alcohols, particularly alkyl alcohols, alkoxy, acyl, cyano, nitro, epoxy, haloalkyl groups, halogen, hydrogen and hydroxyl; R 12 is selected from the group consisting of aliphatic groups, particularly lower alkyl groups, aliphatic alcohols, particularly alkyl alcohols, carboxylic acids and hydrogen. Compositions comprising effective amounts of such compounds also are described. These compounds and compositions can be used in a method for inhibiting the proliferation of living cells in a subject comprising administering an effective amount of the compound(s), or composition(s) comprising the compound(s), to a subject to inhibit the proliferation of living cells, such as neoplastic cells.

  描述了一类新型的细胞周期依赖性激酶抑制剂，这些抑制剂在人类肿瘤细胞系实验中还具有抗增殖活性。其中大多数化合物符合以下公式：其中A是氧或硫，通过单键或双键与右侧连接；R2选择自氢、芳基、较低的脂肪基取代物，特别是烷基和较低的烷基酯；R4-R7独立地选择自烷氧基、氨基、酰基、脂肪基取代物，特别是烷基、烯基和炔基取代物、脂肪醇，特别是烷基醇、脂肪腈，特别是烷基腈、氰基、硝基、羧基、卤素、氢、羟基、亚甲基、β-甲基、不饱和酮；R8-R11独立地选择自脂肪基取代物，特别是烷基、烯基和炔基取代物，特别是较低的脂肪基取代物、脂肪醇，特别是烷基醇、烷氧基、酰基、氰基、硝基、环氧基、卤代烷基、卤素、氢和羟基；R12选择自脂肪基，特别是较低烷基，脂肪醇，特别是烷基醇，羧酸和氢。还描述了包含这些化合物有效量的组合物。这些化合物和组合物可用于抑制体内细胞增殖的方法，包括向受体内施用化合物的有效量或含有该化合物的组合物的有效量，以抑制细胞增殖，如肿瘤细胞。
• Use of paullone derivatives for making medicines
  申请人：——

  公开号：US20030181439A1

  公开（公告）日：2003-09-25

  The invention concerns the use for producing of GSK-3&bgr; inhibiting medicines from paullone derivatives. The invention is useful for treating pathologies involving GSK-3&bgr; and CDK5.

  这项发明涉及利用paullone衍生物生产抑制GSK-3β药物的用途。该发明对治疗涉及GSK-3β和CDK5的病理状况有用。
• Epoxide-containing side chains enhance antiproliferative activity of paullones
  作者：Xu Xie、Thomas Lemcke、Rick Gussio、Daniel W. Zaharevitz、Maryse Leost、Laurent Meijer、Conrad Kunick

  DOI：10.1016/j.ejmech.2005.02.004

  日期：2005.7

  syntheses were accomplished applying Stille coupling for the introduction of unsaturated side chains into the 2-position of the paullones and subsequently employing a hydrogen peroxide/nitrile mixture for the epoxidation of C,C-double bonds.

  将带有环氧化物基团的侧链引入kenpaullone和9-三氟甲基paullone的分子支架中，可提高新型衍生物对人肿瘤细胞系的抗增殖活性。合成是通过应用Stille偶联将不饱和侧链引入paullones的2位而完成的，随后使用过氧化氢/腈混合物进行C，C-双键的环氧化。
• [EN] FUSED AZEPINONE CYCLIN DEPENDENT KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES DEPENDANTES DE LA CYCLINE SOUS FORME D'AZEPINONE FUSIONNEE
  申请人：US HEALTH

  公开号：WO1999065910A1

  公开（公告）日：1999-12-23

  A new class of cyclin dependent kinase inhibitors that also have antiproliferative activity in human tumor cell line assays are described. Most of these compounds satisfy formula (I); wherein A is oxygen or sulfur coupled to the right by a single or double bond; R2 is selected from the group consisting of hydrogen, aryl, lower aliphatic substituents, particularly alkyl and lower alkyl ester; R4-R7 are independently selected from the group consisting of alkoxy, amino, acyl, aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, aliphatic alcohols, particularly alkyl alcohols, aliphatic nitriles, particularly alkyl nitriles, cyano, nitro, carboxyl, halogen, hydrogen, hydroxyl, imino, and α, β unsaturated ketones; R8-R11 are independently selected from the group consisting of aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, particularly lower aliphatic substituents, aliphatic alcohols, particularly alkyl alcohols, alkoxy, acyl, cyano, nitro, epoxy, haloalkyl groups, halogen, hydrogen and hydroxyl; R12 is selected from the group consisting of aliphatic groups, particularly lower alkyl groups, aliphatic alcohols, particularly alkyl alcohols, carboxylic acids and hydrogen. Compositions comprising effective amounts of such compounds also are described. These compounds and compositions can be used in a method for inhibiting the proliferation of living cells in a subject comprising administering an effective amount of the compound(s), or composition(s) comprising the compound(s), to a subject to inhibit the proliferation of living cells, such as neoplastic cells.

  描述了一类新型的细胞周期依赖性激酶抑制剂，这些化合物在人类肿瘤细胞系试验中也具有抗增殖活性。其中大多数化合物满足公式（I）; 其中A是氧或硫，通过单键或双键与右侧相连; R2选自氢、芳基、较低的脂肪基取代基，特别是烷基和较低的烷基酯基; R4-R7独立地选自烷氧基、氨基、酰基、脂肪基取代基，特别是烷基、烯基和炔基取代基，脂肪醇，特别是烷基醇，脂肪腈，特别是烷基腈，氰基，硝基，羧基，卤素，氢，羟基，亚氨基和α，β不饱和酮; R8-R11独立地选自脂肪基取代基，特别是烷基、烯基和炔基取代基，特别是较低的脂肪基取代基，脂肪醇，特别是烷基醇，烷氧基，酰基，氰基，硝基，环氧基，卤代烷基，卤素，氢和羟基; R12选自脂肪基，特别是较低的烷基，脂肪醇，特别是烷基醇，羧酸和氢的群。还描述了包含这些化合物有效量的组合物。这些化合物和组合物可用于抑制受试主体中细胞增殖的方法，包括向受试主体施用化合物的有效量或含有化合物的组合物的有效量，以抑制细胞增殖，例如肿瘤细胞。