1-[5-(benzyloxy)-1H-indol-3-yl]-2-chloroethanone | 37800-46-7

• 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: 1-[5-(benzyloxy)-1H-indol-3-yl]-2-chloroethanone
• 英文别名: 1-(5-benzyloxy-1H-indol-3-yl)-2-chloro-ethanone；3-(chloroacetyl)-5-(benzyloxy)indole；3-chloroacetyl-5-(benzyloxy)indole；Chlormethyl-3-(5-benzyloxy)-indolylketon；2-chloro-1-(5-phenylmethoxy-1H-indol-3-yl)ethanone
• CAS: 37800-46-7
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: YDWQITSRZHKDKB-UHFFFAOYSA-N

物化性质

• 沸点：
  508.5±40.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[5-(benzyloxy)-1H-indol-3-yl]-2-chloroethanone 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 氢气 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 2.0h， 生成 tert-butyl 3-(2-amino-1,1-difluoro-ethyl)-5-hydroxy-indole-1-carboxylate
  参考文献：
  名称：

  Syntheses of β,β-Difluorotryptamines

  摘要：

  Tryptamines disubstituted at the beta-position with fluorine have been synthesized as part of our research program to study the effects of fluorine substitution on the biological activities of neuroactive amines. Treatment of N-Boc-3-azidoacetyl indoles, prepared from readily available 2-chloracetylindoles, with dimethoxyethylamino sulfurtrifluoride produced the corresponding 3-(2-azido-1,1-difluoroethyl)indoles. Reduction of the azide to amine with hydrogen over Pd-C and careful removal of the N-Boc protecting group produced beta,beta-difluorotryptamines.

  DOI：

  10.1021/jo020731c
• 作为产物：
  描述：

  5-羟基吲哚 在 四丁基氯化铵 、 sodium hydroxide 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.5h， 生成 1-[5-(benzyloxy)-1H-indol-3-yl]-2-chloroethanone
  参考文献：
  名称：

  Indole derivatives as dual-effective agents for the treatment of neurodegenerative diseases: Synthesis, biological evaluation, and molecular modeling studies

  摘要：

  Several indole derivatives, that were highly potent ligands of GluN2B-subunit-containing N-methyl-D-aspartate (NMDA) receptor, also demonstrated antioxidant properties in ABTS method. In particular, the 2-(4-benzylpiperidin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone (1) proved to be a dual-effective neuroprotective agent. With the aim to increase the antioxidant properties we added a catechol moiety onto piperidine moiety. The designed hybrid derivative 3,4-dihydroxy-N-[1-[2-(5-hydroxy-1H-indol-3-yl)-2-oxoethyl]piperidin-4-yl]benzamide (10) was the most effective antioxidant agent (>94.1 +/- 0.1% of inhibition at 17 mu M) and showed GluN2B/NMDA receptor affinity at low micromolar concentration (IC50 0.66 mu M). By means of computational studies we explored the effect of the presence of this antioxidant fragment during the recognition process to binding pocket. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.044

文献信息

• [EN] SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN<br/>[FR] INHIBITEURS DE SÉPIAPTÉRINE RÉDUCTASE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：HERCULES TECHNOLOGY MAN CO V INC

  公开号：WO2011047156A1

  公开（公告）日：2011-04-21

  Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and prodrugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain).

  本文介绍的是对丝氨酸脱氢酶（SPR）的小分子杂环抑制剂，以及它们的前药和药用盐。还包括这些化合物的药物组合物以及这些化合物用于治疗或预防疼痛（如炎症性疼痛、伤害性疼痛、功能性疼痛和神经病理性疼痛）的用途。
• Topsentin compounds effective against viruses and certain tumors
  申请人：Harbor Branch Oceanographic Institution, Inc.

  公开号：US04866084A1

  公开（公告）日：1989-09-12

  A new class of novel, biologically active bisindole alkaloid compounds, which have been named topsentins, pharmaceutical compositions containing them, methods of producing the compounds and methods of using them are disclosed. This new class of compounds has the generic formula: ##STR1## R.sup.1-8 are the same or different selected from --H, --OH, halogen, --R, --OR, --OCOR, or --OA; Y is the single group --O, or two groups, same or different, selected from --H, --OH, --OR, or --OCOR with the provision that Y shall not be two --OH groups; Z are the same or different selected from --H, --R; R is C1-5 alkyl and A is --R--phenyl. The compounds are antiviral agents and antitumor agents which are effective against specific tumors.

  揭示了一类新型的生物活性双吲哚生物碱化合物，被命名为topsentins，包含它们的药物组合物，生产这些化合物的方法以及使用它们的方法。这类新化合物具有通用结构式：##STR1## R.sup.1-8 可选择相同或不同的 --H、--OH、卤素、--R、--OR、--OCOR 或 --OA；Y 是单一基团 --O，或两个基团，相同或不同，选择自 --H、--OH、--OR 或 --OCOR，但 Y 不应为两个 --OH 基团；Z 可选择相同或不同的 --H、--R；R 为 C1-5 烷基，A 为 --R--苯基。这些化合物是抗病毒剂和抗肿瘤剂，对特定肿瘤具有有效作用。
• Antiulcer agents. 4-Substituted 2-guanidinothiazoles: reversible, competitive, and selective inhibitors of gastric H+,K+-ATPase
  作者：John L. LaMattina、Peter A. McCarthy、Lawrence A. Reiter、William F. Holt、Li An Yeh

  DOI：10.1021/jm00164a012

  日期：1990.2

  A series of 4-substituted 2-guanidinothiazoles has been found to inhibit the gastric proton-pump enzyme H+,K(+)-ATPase. In general, these compounds were reversible inhibitors of canine gastric H+,K(+)-ATPase, competitive at the K+ site, and selective relative to canine renal Na+,K(+)-ATPase. Structure-activity relationship (SAR) studies on this series revealed no general replacement for the guanidinothiazole. On the other hand, use of pyrrolyl, phenyl, and indolyl groups as the C-4 substituent yielded active compounds. Extensive studies of substitution patterns on these 4-aryl groups led to more active compounds, but no consistent SAR became apparent. Monosubstitution of the guanidine and substitution of the thiazole at C-5 both often led to increased activity, but combining these changes generated compounds less active than the parents. Despite 100-fold improvement in in vitro inhibitory potency, only a 3-fold increase in gastric antisecretory activity in rats was observed for these agents.
• Topsentin, bromotopsentin, and dihydrodeoxybromotopsentin: antiviral and antitumor bis(indolyl)imidazoles from Caribbean deep-sea sponges of the family Halichondriidae. Structural and synthetic studies
  作者：Shinji Tsujii、Kenneth L. Rinehart、Sarath P. Gunasekera、Yoel Kashman、Susan S. Cross、May S. Lui、Shirley A. Pomponi、M. Cristina Diaz

  DOI：10.1021/jo00258a009

  日期：1988.11
• TSUJII, SHINJI;RINEHART, KENNETH L.;GUNASEKERA, SARATH P.;KASHMAN, YOEL;C+, J. ORG. CHEM., 53,(1988) N 23, C. 5446-5453
  作者：TSUJII, SHINJI、RINEHART, KENNETH L.、GUNASEKERA, SARATH P.、KASHMAN, YOEL、C+

  DOI：——

  日期：——