5-Propylisatin | 131609-60-4

• 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-Propylisatin
• 英文别名: 5-propylindole-2,3-dione；5-propyl-2,3-indoledione；5-Propylindoline-2,3-dione；5-propyl-1H-indole-2,3-dione
• CAS: 131609-60-4
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD09738121
• 分子量: 189.214
• InChiKey: FBYONXZHXASRNB-UHFFFAOYSA-N

物化性质

• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  5-Propylisatin 在 potassium chloride 、 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 以29%的产率得到5-Propyl-2-amino-benzoesaeure
  参考文献：
  名称：

  基于可溶液加工的二苯并四硫富瓦烯衍生物的有机场效应晶体管

  摘要：

  基于烷基取代的二苯并四硫富瓦烯 (DBTTF) 的有机场效应晶体管是通过溶液工艺制造的。具有丁基或更长烷基基团的分子是立...

  DOI：

  10.1246/cl.2009.200
• 作为产物：
  描述：

  水合氯醛 、 对丙基苯胺 在 盐酸 、 盐酸羟胺 、 sodium sulfate 、 硫酸 作用下， 以 水 为溶剂， 反应 0.02h， 以100%的产率得到5-Propylisatin
  参考文献：
  名称：

  基于可溶液加工的二苯并四硫富瓦烯衍生物的有机场效应晶体管

  摘要：

  基于烷基取代的二苯并四硫富瓦烯 (DBTTF) 的有机场效应晶体管是通过溶液工艺制造的。具有丁基或更长烷基基团的分子是立...

  DOI：

  10.1246/cl.2009.200

文献信息

• Phosphodiesterase inhibitors
  申请人：LES LABORATOIRES BEECHAM S.A.

  公开号：EP0381374A1

  公开（公告）日：1990-08-08

  A compound of formula (I), or a pharmaceutically acceptable salt thereof: in which, R₁ is hydrogen, C₁₋₆ alkyl or CH₂OR₆; R₂ is hydrogen or C₁₋₆ alkyl; R₃ is hydrogen or C₁₋₆ alkyl; each of W and Z, which are different, represents -CR₄R₅- or -(CRxRy)n-, in which, R₄ is hydrogen, C₁₋₃ alkyl, C₁₋₃ alkylthio, C₁₋₃ alkoxy or C₁₋₆ alkyl phenyl; R₅ is C₁₋₃ alkyl, C₁₋₃ alkylthio, C₁₋₃ alkoxy, phenyl, substituted phenyl, C₃₋₆ cycloalkyl, phenylthio, C₁₋₆ alkyl phenyl, halo-substituted benzyl, or heteroaryl; or together R₄ and R₅ form a 3 to 6 membered carbocyclic ring, or a heterocyclic ring containing one or two ring oxygen, nitrogen or sulphur atoms, or R₄ and R₅ together form an oxo or methylene group; each of Rx and Ry is hydrogen or C₁₋₃ alkyl; n is zero or 1; R₆ is phenyl substituted aminocarbonyl, C₁₋₆ alkoxy carbonyl-C₁₋₆ alkyl, phenyl-C₁₋₆ alkyl, phenyl, C₃₋₆ cycloalkylcarbonyl, C₃₋₆ cycloalkylcarbonyl-C₁₋₆ alkyl, C₃₋₆ cycloalkyl C₁₋₆ alkyl; C₁₋₆ alkylthiocarbonyl; halo-substituted C₁₋₆ alkoxycarbonyl; C₁₋₆ alkoxy C₁₋₆ alkyleneoxycarbonyl; C₁₋₆ alkylthio C₁₋₆ alkyleneoxycarbonyl; C₁₋₆ alkoxythiocarbonyl; C₃₋₆ cycloalkyloxycarbonyl; cyano substituted C₁₋₆ alkoxycarbonyl; di-C₁₋₆ alkylphosphonate; C₁₋₆ alkenyloxycarbonyl; or R₆ is hydrogen when R₅ is phenyl, C₃₋₆ cycloalkyl, phenylthio, C₁₋₆ alkylphenyl or halo-substituted benzyl; R₆ is benzoyl or aminobenzoyl when R₄ and R₅ form a C₃₋₆ cycloalkyl ring; R₇ is hydrogen, C₁₋₆ alkyl or halogen; X is oxygen or sulphur; and A is sulphur, oxygen or -NH-, is useful for the treatment of heart disease.

  式（I）的化合物，或其药学上可接受的盐：其中，R₁为氢，C₁₋₆烷基或CH₂OR₆；R₂为氢或C₁₋₆烷基；R₃为氢或C₁₋₆烷基；W和Z中的每一个，它们不同，代表-CR₄R₅-或-(CRxRy)n-，其中，R₄为氢，C₁₋₃烷基，C₁₋₃烷基硫，C₁₋₃烷氧基或C₁₋₆烷基苯基；R₅为C₁₋₃烷基，C₁₋₃烷基硫，C₁₋₃烷氧基，苯基，取代苯基，C₃₋₆环烷基，苯硫基，C₁₋₆烷基苯基，卤代苄基或杂环烷基；或者R₄和R₅一起形成3到6成员的碳环，或者含有一个或两个环氧原子、氮原子或硫原子的杂环；或者R₄和R₅一起形成氧或亚甲基基团；Rx和Ry中的每一个为氢或C₁₋₃烷基；n为零或1；R₆为苯基取代氨基甲酰基，C₁₋₆烷氧基甲酰基-C₁₋₆烷基，苯基-C₁₋₆烷基，苯基，C₃₋₆环烷基甲酰基，C₃₋₆环烷基甲酰基-C₁₋₆烷基，C₃₋₆环烷基C₁₋₆烷基；C₁₋₆烷基硫代甲酰基；卤代C₁₋₆烷氧基甲酰基；C₁₋₆烷氧基-C₁₋₆烷基氧基甲酰基；C₁₋₆烷基硫基-C₁₋₆烷基氧基甲酰基；C₁₋₆烷氧基硫代甲酰基；C₃₋₆环烷氧基甲酰基；氰基取代C₁₋₆烷氧基甲酰基；二C₁₋₆烷基膦酸酯；C₁₋₆烯氧基甲酰基；或者当R₅为苯基，C₃₋₆环烷基，苯硫基，C₁₋₆烷基苯基或卤代苄基时，R₆为氢；当R₄和R₅形成C₃₋₆环烷基环时，R₆为苯甲酰基或氨基苯甲酰基；R₇为氢，C₁₋₆烷基或卤素；X为氧或硫；A为硫，氧或-NH-，用于治疗心脏病。
• Discovery of Indolone Acetamides as Novel SV2A Ligands with Improved Potency Toward Seizure Suppression
  作者：Anne Frycia、Jean-Philippe Starck、Sophie Jadot、Bénédicte Lallemand、Karine Leclercq、Patrick Lo Brutto、Alain Matagne、Valérie Verbois、Joël Mercier、Benoit Kenda

  DOI：10.1002/cmdc.200900436

  日期：2010.2.1

  Capitalizing on the proven clinical efficacy of levetiracetam as an antiepileptic drug, a drug discovery program lead to the identification of a new generation of SV2A ligands with equal or better tolerability profiles than levetiracetam, and improved potency toward seizure suppression in animal models.

  利用左乙拉西坦作为抗癫痫药的久经验证的临床功效，药物发现计划导致鉴定出与左乙拉西坦具有相同或更好耐受性的新一代SV2A配体，并提高了在动物模型中抑制癫痫发作的能力。
• 8-Methyltryptanthrin-Induced Differentiation of P19CL6 Embryonal Carcinoma Cells into Spontaneously Beating Cardiomyocyte-like Cells
  作者：Kazuhiko Seya、Asako Yamaya、Sayuri Kamachi、Mana Murakami、Haruo Kitahara、Jun Kawakami、Ken Okumura、Manabu Murakami、Shigeru Motomura、Ken-Ichi Furukawa

  DOI：10.1021/np500108r

  日期：2014.6.27

  Enhancement of cardiac differentiation is critical to stem cell transplantation therapy for severe ischemic heart disease. The aim of this study was to investigate whether several derivatives of tryptanthrin (1), extracted from the medicinal plant Polygonum tinctorium, induce the differentiation of P19CL6 mouse embryonal carcinoma cells into beating cardiomyocyte-like cells. P19CL6 cells were cultured in α-MEM supplemented with 10% FBS including a test compound or vehicle. Drug-induced differentiation was assessed by measuring the number of beating and nonbeating aggregates and the area of beating aggregates, and the expression of genes involved in cardiac differentiation was evaluated by real-time PCR. A 1 μM concentration of 8-methyltryptanthrin (2) induced the differentiation of P19CL6 cells into cardiomyocyte-like cells to a significantly greater degree than 1% dimethyl sulfoxide (DMSO), a conventional differentiation inducer of P19CL6 cells. Furthermore, 2 strongly increased both the number and the area of spontaneously beating aggregates in comparison with DMSO. Two distinct genes of the calcium channel family, Cav1.2 and Cav3.1, underlying cardiac automaticity were significantly expressed in the presence of 2. Gap junction genes GJA1 and GJA5 contributing to the synchronized contraction of the myocardium were also induced significantly by 2. These results suggest that 2 successfully differentiated P19CL6 cells into spontaneously beating cardiomyocyte-like cells by activating the gene expression of pacemaker channels and gap junctions.