Z-indanylideneacetic acid | 308339-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: Z-indanylideneacetic acid
• 英文别名: 2-(1-oxo-2,3-dihydro-(1H)-2-indanyliden)acetic acid；(2Z)-2-(3-oxo-1H-inden-2-ylidene)acetic acid
• CAS: 308339-66-4
• 化学式: C₁₁H₈O₃
• 分子量: 188.183
• InChiKey: CRIAYPLBQCVXMB-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-indanylideneacetic acid 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 为溶剂， 以77%的产率得到(1-oxo-2-indanyl)acetic acid
  参考文献：
  名称：

  Dose−Response of Seeds of the Parasitic Weeds Striga and Orobanche toward the Synthetic Germination Stimulants GR 24 and Nijmegen 1

  摘要：

  Striga and Orobanche seeds germinate in response to a host-derived germination stimulant. Dose-response curves of the synthetic strigolactone analogues GR 24 and Nijmegen 1 were determined, and their activities were compared to that of the naturally occurring stimulant sorgolactone. Typical sigmoidal curves were obtained. ED50 values for GR 24 were in the order of 10(-9)-10(-8) mol/L; for Nijmegen 1 these values were 3 orders of magnitude higher. Both synthetic stimulants are appreciably active at low concentrations and merit investigation as agents for the suicidal germination approach (i.e., treatment of the soil with stimulant in the absence of a host).

  DOI：

  10.1021/jf981006z
• 作为产物：
  描述：

  2-(1,3-二氢-1-氧代-2H-茚-2-亚基)乙酸 以 乙腈 为溶剂， 生成 (E)-2-(1-oxo-1H-inden-2(3H)-ylidene)acetic acid 、 Z-indanylideneacetic acid
  参考文献：
  名称：

  1-氧代-环烷基-2-亚基乙酸的结构和反应性。阿1 H NMR，建模与光化学研究

  摘要：

  在脂肪族环的大小和缩合的不饱和环的性质上不同的四种1-氧代-环烷烃基-2-亚烷基乙酸对肼具有不同的反应性，仅在一种情况下导致所需的三环吡啶并哒嗪酮。观察到的行为差异不能归因于四种酸的环外双键的不同构型：1 H NMR实验结合UV光解表明，所有化合物均以E形式制备，并且在不存在E的情况下稳定。灯和催化剂。光化学获得的Z异构体显示出随着脂肪族环的尺寸增加而形成三环内酯的趋势增加。E和E的理论结构分析Z异构体，三环内酯和与肼反应的一些假设中间体表明，脂族环的大小和相关的柔韧性对于调节这些化合物形成三环产物的能力至关重要。

  DOI：

  10.1016/s0040-4020(00)00662-1

文献信息

• [EN] NOVEL DERIVATIVES OF A FIVE-MEMBERED RING FUSED BENZENE, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESS FOR PREPARING SAME<br/>[FR] NOUVEAUX DERIVES DE BENZENE A CYCLES PENTAGONAUX CONDENSES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, ET LEUR PROCEDE DE PREPARATION
  申请人：RICHTER GEDEON VEGYÉSZETI GYÁR RT.

  公开号：WO1994014788A1

  公开（公告）日：1994-07-07

  (EN) The invention relates to novel, therapeutically active acid, salt, ester and amide derivatives of a 5-membered ring fused benzene of formula (I), wherein R is selected from hydroxy, (C1-4)alkoxycarbonylmethoxy, (C1-4)alkylamino, cyclohexylamino; phenylamino optionally substituted by halogen; (C1-4)alkoxycarbonylmethylamino, 1-(C1-4)alkoxycarbonyl-2-phenylethylamino, pyrrolidino and N-(C1-4)alkoxycarbonylpiperazino; and X stands for oxygen or methylene, with the proviso that X means oxygen when R stands for hydroxy; and their salts formed with H2 receptor antagonists, when X means oxygen and R stands for hydroxy, as well as pharmaceutical compositions containing the above compounds. The invention relates also to a process for the preparation of the above compounds and compositions. The compounds of formula (I) show significant gastrocytoprotective and gastric acid secretion inhibitory activities. In addition, they possess an antibacterial activity against the pathogenic bacterial strain Helicobacter pylori. Thus, they are useful for the prevention and/or healing of various ulcerative diseases of the digestive system (oesophagus, stomach and duodenum).(FR) Nouveaux dérivés, à activité thérapeutique et sous forme d'acide, de sel, d'ester et d'amide, d'un benzène à cycles pentagonaux condensés, répondant à la formule (I), dans laquelle R est sélectionné parmi hydroxy, alcoxy(C1-4)carbonylméthoxy, alkyl(C1-4)amino, cyclohéxylamino; phénylamino éventuellement substitué par halogène; alcoxy(C1-4)carbonylméthylamino, 1-alcoxy(C1-4)carbonyl-2-phényléthylamino, pyrrolidino et N-alcoxy(C1-4)carbonylpipérazino; et X représente oxygène ou méthylène, à condition que X représente oxygène lorsque R représente hydroxy; leurs sels formés avec des antagonistes du récepteur de H2, lorsque X représente oxygène et R représente hydroxy; et compositions pharmaceutiques contenant les composés précités. On a également prévu un procédé de préparation des composés et compositions précités. Les composés de la formule (I) présentent des activités significatives de gastro-cytoprotection et d'inhibition de la sécrétion d'acide gastrique. En outre, ils présentent une activité antibactérienne dirigée contre la souche bactérienne pathogène $i(Helicobacter pylori). De ce fait, ils sont utilisables dans la prévention et/ou le traitement de diverses maladies ulcératives de l'appareil digestif (÷sophage, estomac et duodénum).
• Structures and Reactivities of 1-Oxo-cycloalkan-2-ylideneacetic Acids. A 1H NMR, Modelling and Photochemical Study
  作者：Stefano Ghelli、M Paola Costi、Lucio Toma、Daniela Barlocco、Glauco Ponterini

  DOI：10.1016/s0040-4020(00)00662-1

  日期：2000.9

  tendency to form tricyclic lactones with increasing size of the aliphatic ring. A theoretical structural analysis of the E and Z isomers, the tricyclic lactones and some of the hypothetical intermediates of the reaction with hydrazine suggests the size of the aliphatic ring and the associated flexibility to be crucial in modulating the ability of these compounds to form tricyclic products.

  在脂肪族环的大小和缩合的不饱和环的性质上不同的四种1-氧代-环烷烃基-2-亚烷基乙酸对肼具有不同的反应性，仅在一种情况下导致所需的三环吡啶并哒嗪酮。观察到的行为差异不能归因于四种酸的环外双键的不同构型：1 H NMR实验结合UV光解表明，所有化合物均以E形式制备，并且在不存在E的情况下稳定。灯和催化剂。光化学获得的Z异构体显示出随着脂肪族环的尺寸增加而形成三环内酯的趋势增加。E和E的理论结构分析Z异构体，三环内酯和与肼反应的一些假设中间体表明，脂族环的大小和相关的柔韧性对于调节这些化合物形成三环产物的能力至关重要。
• Dose−Response of Seeds of the Parasitic Weeds <i>Striga</i> and <i>Orobanche</i> toward the Synthetic Germination Stimulants GR 24 and Nijmegen 1
  作者：S. C. M. Wigchert、E. Kuiper、G. J. Boelhouwer、G. H. L. Nefkens、J. A. C. Verkleij、B. Zwanenburg

  DOI：10.1021/jf981006z

  日期：1999.4.1

  Striga and Orobanche seeds germinate in response to a host-derived germination stimulant. Dose-response curves of the synthetic strigolactone analogues GR 24 and Nijmegen 1 were determined, and their activities were compared to that of the naturally occurring stimulant sorgolactone. Typical sigmoidal curves were obtained. ED50 values for GR 24 were in the order of 10(-9)-10(-8) mol/L; for Nijmegen 1 these values were 3 orders of magnitude higher. Both synthetic stimulants are appreciably active at low concentrations and merit investigation as agents for the suicidal germination approach (i.e., treatment of the soil with stimulant in the absence of a host).