2-chloro-10-propyl-10H-phenothiazine | 92549-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-chloro-10-propyl-10H-phenothiazine
• 英文别名: 2-Chloro-10-propylphenothiazine
• CAS: 92549-87-6
• 化学式: C₁₅H₁₄ClNS
• 分子量: 275.802
• InChiKey: PDPYGLOOZZBBFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-10-propyl-10H-phenothiazine 、 4-溴苯磺酰氯 在 copper(l) iodide 、 lithium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以54%的产率得到7-((4-bromophenyl)sulfonyl)-2-chloro-10-propyl-10H-phenothiazine
  参考文献：
  名称：

  Non-directed copper-catalyzed regioselective C–H sulfonylation of phenothiazines

  摘要：

  苯并噻嗪的C3磺酰化的简单通用程序是通过CuI/Li₂CO₃催化的芳基/烷基磺酰氯转化而开发的。

  DOI：

  10.1039/c9ob00705a
• 作为产物：
  描述：

  2-氯吩噻嗪 、 溴丙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以75%的产率得到2-chloro-10-propyl-10H-phenothiazine
  参考文献：
  名称：

  Non-directed copper-catalyzed regioselective C–H sulfonylation of phenothiazines

  摘要：

  苯并噻嗪的C3磺酰化的简单通用程序是通过CuI/Li₂CO₃催化的芳基/烷基磺酰氯转化而开发的。

  DOI：

  10.1039/c9ob00705a

文献信息

• Reengineered tricyclic anti-cancer agents
  作者：David B. Kastrinsky、Jaya Sangodkar、Nilesh Zaware、Sudeh Izadmehr、Neil S. Dhawan、Goutham Narla、Michael Ohlmeyer

  DOI：10.1016/j.bmc.2015.07.007

  日期：2015.10

  The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacological assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent molecules. Its effects were attributed to concomitant negative regulation of PI3K-AKT and RAS-ERK signaling. (C) 2015 Elsevier Ltd. All rights reserved.
• TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS
  申请人：Mount Sinai School of Medicine

  公开号：EP2744808A2

  公开（公告）日：2014-06-25
• CONJUGATES OF HUPERZINE AND ANALOGS THEREOF
  申请人：INSERO HEALTH INC.

  公开号：US20150191430A1

  公开（公告）日：2015-07-09

  Compounds and compositions for treating neurodegenerative diseases are described. The compounds include a therapeutic agent covalently linked with huperzine or an analog thereof through a linker. Methods of preparing the compounds are described. Methods of treating a neurodegenerative disease by administering compounds and compositions including a therapeutic agent covalently linked with huperzine or an analog thereof are described. Methods for delivering a therapeutic agent by administering the therapeutic agent covalently linked to huperzine or an analog thereof are described.
• [EN] HEPATITIS C VIRUS ENTRY INHIBITORS<br/>[FR] INHIBITEURS DE LA PÉNÉTRATION DU VIRUS DE L'HÉPATITE C
  申请人：IMMUSOL INC

  公开号：WO2008021745A2

  公开（公告）日：2008-02-21

  [EN] The present invention relates to the use of tricyclic diphenylamine derivative compounds for prevention and/or treatment of Hepatitis C virus (HCV) infection by inhibiting HCV entry into permissive cells.
  [FR] La présente invention concerne l'utilisation de composés dérivés de la diphénylamine tricyclique pour la prévention et/ou le traitement d'une infection par le virus de l'hépatite C (Hepatitis C Virus : HCV) en inhibant la pénétration du HCV dans les cellules permissives.
• [EN] TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS<br/>[FR] COMPOSÉS TRICYCLIQUES EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：MT SINAI SCHOOL OF MEDICINE

  公开号：WO2013025882A2

  公开（公告）日：2013-02-21

  Tricyclic chemical modulators of FOXO transcription factor proteins are disclosed. The compounds are useful to treat cancer, age-onset proteotoxicity, stress-induced depression, inflammation, and acne. The compounds are of phenothiazine, dibenzoazepine and annulene and similar genera.