7-羧基吲哚啉 | 15861-40-2

• 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
• 中文名称: 7-羧基吲哚啉
• 英文名称: indoline-7-carboxylic acid
• 英文别名: Indolin-7-carbonsaeure；2,3-dihydro-1H-indole-7-carboxylic acid
• CAS: 15861-40-2
• 化学式: C₉H₉NO₂
• mdl: MFCD11617212
• 分子量: 163.176
• InChiKey: GDNYELSKMFYCBB-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C (decomp)
• 沸点：
  356.3±31.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-羧基吲哚啉 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 4.0h， 以52%的产率得到7-吲哚甲酸
  参考文献：
  名称：

  Synthesis and Evaluation of Heterocyclic Carboxamides as Potential Antipsychotic Agents

  摘要：

  Heterocyclic analogues of 1192U90, 2-amino-N-(4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)- butyl)benzamide hydrochloride (1), were prepared and evaluated as potential antipsychotic agents. These analogues were evaluated in vitro for their binding to the dopamine D-2, serotonin 5-HT2, and serotonin 5-HTL(1a) receptors and in vivo for their ability to antagonize the apomorphine-induced climbing response in mice. Nine different types of heterocyclic carboxamides were studied in this investigation (i.e., pyridine-, thiophene-, benzothiophene-, quinoline-, 1,2,3,4-tetrahydroquinoline-,2,3-dihydroindole-, indole-, benzimidazole-, and indazolecarbox-amides), Two derivatives exhibited potent in vivo activities comparable to 1: 3-amino-N-(4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl)-2-pyridinecarboxamide (16) and 3-amino-N-(4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl)-2-thiophenecarboxamide (29). Furthermore, these derivatives were found to be much less active in behavioral models predictive of extrapyramidal side effects than in the mouse climbing assay, which predicts antipsychotic activity. Carboxamides 16 and 29 were selected for further evaluation as potential backup compounds to 1.

  DOI：

  10.1021/jm9603375
• 作为产物：
  描述：

  3-烯丙基-2-羟基苯甲酸甲酯 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 氯化亚砜 、 二甲基硫 、 sodium hydride 、 臭氧 、 二异丙胺 、 肼 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 87.0h， 生成 7-羧基吲哚啉
  参考文献：
  名称：

  Nucleophilic annulations of aromatics. Novel route to benzo-fused ring systems via oxazoline activation

  摘要：

  DOI：

  10.1021/jo00317a027

文献信息

• Studies on a Novel, Potent and Orally Effective Cholecystokinin A Antagonist, FK-480. Synthesis and Structure-Activity Relationships of FK-480 and Related Compounds.
  作者：Yoshinari SATOH、Teruaki MATSUO、Hajime SOGABE、Harunobu ITOH、Toshiji TADA、Takayoshi KINOSHITA、Keizou YOSHIDA、Takao TAKAYA

  DOI：10.1248/cpb.42.2071

  日期：——

  We prepared various novel tricyclic 1, 4-benzodiazepine derivatives as cholecystokinin (CCK) A antagonists, which were evaluated preliminarily for inhibition of <125>I-CCK-8 binding to rat pancreatic membranes in vitro and inhibiting effect on CCK-8-induced inhibition of charcoal meal gastric emptying in mice. On the basis of structure-activity relationship (SAR) studies, as well as the stability and availability of the starting materials of those compounds, (S)-N-[1-(2-fluorophenyl)-3, 4, 6, 7-tetrahydro-4-oxo-pyrrolo[3, 2, 1-jk][1, 4]benzodiazepin-3-yl]-1H-indole-2-carboxamide (9f, FK-480) was selected as a candidate compound for further evaluation. The absolute configuration of the precursor of FK-480, (3S)-amino-1, 4-benzodiazepine derivative ((S)-8a, R1=F) was determined by an X-ray crystallographic study of its ureido derivative with (S)-α-methylbenzyl isocyanate.FK-480 is now undergoing clinical studies for the treatment of chronic pancreatitis.

  我们制备了多种新型三环1,4-苯并二氮杂䓬衍生物作为胆囊收缩素（CCK）A受体拮抗剂，并初步评估了它们对<125>I-CCK-8与大鼠胰腺膜体外结合的抑制作用以及对CCK-8诱导的小鼠活性炭餐胃排空的抑制作用。基于构效关系（SAR）研究以及这些化合物的起始原料的稳定性和可获得性，我们选择了(S)-N-[1-(2-氟苯基)-3,4,6,7-四氢-4-氧代-吡咯并[3,2,1-jk][1,4]苯并二氮杂䓬-3-基]-1H-吲哚-2-甲酰胺（9f, FK-480）作为候选化合物进行进一步评估。通过与(S)-α-甲基苄基异氰酸酯的脲基衍生物的X射线晶体学研究，确定了FK-480前体(3S)-氨基-1,4-苯并二氮杂䓬衍生物（(S)-8a, R1=F）的绝对构型。FK-480目前正在进行治疗慢性胰腺炎的临床研究。
• Indole, indazole and indoline derivatives as CETP inhibitors
  申请人：Conte-Mayweg Aurelia

  公开号：US20060030613A1

  公开（公告）日：2006-02-09

  The present invention relates to compounds of formula (I): wherein —X—Y—, R 1 to R 11 and n are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are mediated by CETP inhibitors.

  本发明涉及以下式(I)的化合物： 其中-X-Y-, R1至R11和n如描述和权利要求中所定义，并且其药学上可接受的盐。这些化合物对于治疗和/或预防通过CETP抑制剂介导的疾病是有用的。
• Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions
  作者：Yuntao Zhou、Irene Piergentili、Jennifer Hong、Michelle P. van der Helm、Mariano Macchione、Yao Li、Rienk Eelkema、Sanzhong Luo

  DOI：10.1021/acs.orglett.0c02128

  日期：2020.8.7

  condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional aniline-catalyzed reaction at neutral conditions. The identified

  酰基hydr的形成已广泛应用于材料科学和生物标记中。然而，它们在中性条件下的凝结速率缓慢，限制了其应用。在本文中，具有电子给体基团的二氢吲哚被报道为新的催化剂支架，其可以通过亚胺离子中间体催化酰基hydr，和肟的形成。在中性条件下，这种新型催化剂显示出比传统苯胺催化反应高出15倍的速率增强。鉴定出的二氢吲哚催化剂已成功应用于水凝胶的形成。
• Tricyclic compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04981847A1

  公开（公告）日：1991-01-01

  Tricyclo benzodiazepines are cholecystokinin antagonists.

  三环苯二氮卓类药物是胆囊收缩素拮抗剂。
• [EN] INSECTICIDAL AMIDES WITH NITROGEN-CONTAINING BENZO-FUSED BICYCLIC RING SYSTEMS<br/>[FR] AMIDES INSECTICIDES COMPRENANT DES SYSTEMES A NOYAU BICYCLIQUE CONDENSES AVEC UN NOYAU BENZENIQUE ET CONTENANT DE L'AZOTE
  申请人：DU PONT

  公开号：WO2003103398A1

  公开（公告）日：2003-12-18

  Disclosed are compounds of Formula I and compounds of Formula II (including all geometric and stereoisomers), N-oxides thereof and salts thereof, certain compositions comprising the compounds of Formula I and/or the compounds of Formula II and certain uses of those compounds and compositions for controlling invertebrate pests INSERT FORMULA I AND II HERE whereinA, B, J, R1, R2, R3, R4, M, M1 and n are as defined in the disclosure.

  揭示了Formula I的化合物和Formula II的化合物（包括所有几何和立体异构体），其N-氧化物和盐，包含Formula I的化合物和/或Formula II的化合物的某些组合物，以及用于控制无脊椎动物害虫的这些化合物和组合物的某些用途，在其中A、B、J、R1、R2、R3、R4、M、M1和n如披露所定义。