benzyl (3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)cyclohexyl)carbamate | 1423078-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: benzyl (3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)cyclohexyl)carbamate
• 英文别名: Benzyl (3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)cyclohexyl)carbamate；benzyl N-[3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)cyclohexyl]carbamate
• CAS: 1423078-37-8
• 化学式: C₂₉H₂₉NO₂
• 分子量: 423.555
• InChiKey: HEWSFYHPIDGLCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl (3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)cyclohexyl)carbamate 在 钯 甲苯 、 乙酸乙酯 、 hexanes 作用下， 以 EtOAc MeOH AcOH 为溶剂， 反应 3.0h， 以to afford the title compound as a white solid (0.326 g, 99%)的产率得到3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)cyclohexanamine
  参考文献：
  名称：

  TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS

  摘要：

  本文披露了三环化学调节剂对FOXO转录因子蛋白的调节作用。这些化合物可用于治疗癌症、年龄相关蛋白质毒性、压力引起的抑郁症、炎症和痤疮。这些化合物属于以下苯硫噻嗪、二苯并氮杂环和环戊烯类似物系列：

  公开号：

  US20140213578A1
• 作为产物：
  描述：

  10,11-二氢二苯并[a,b]环庚烯-5-酮 、 benzyl (3-oxocyclohexyl)carbamate 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以47%的产率得到benzyl (3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)cyclohexyl)carbamate
  参考文献：
  名称：

  Reengineered tricyclic anti-cancer agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.07.007

文献信息

• [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：WO2013025882A3

  公开（公告）日：2013-04-25
• US9540358B2
  申请人：——

  公开号：US9540358B2

  公开（公告）日：2017-01-10
• 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：Ohlmeyer Michael

  公开号：US20140213578A1

  公开（公告）日：2014-07-31

  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 the following phenothiazine, dibenzoazepine and annulene and similar genera:

  本文披露了三环化学调节剂对FOXO转录因子蛋白的调节作用。这些化合物可用于治疗癌症、年龄相关蛋白质毒性、压力引起的抑郁症、炎症和痤疮。这些化合物属于以下苯硫噻嗪、二苯并氮杂环和环戊烯类似物系列：