(E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide | 1453354-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide
• 英文别名: 3-hydroxy-N'-[(1E)-1-(2-hydroxy-5-chlorophenyl)ethylidene]-2-naphthohydrazide；MDG621；N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]-3-hydroxynaphthalene-2-carboxamide
• CAS: 1453354-73-8
• 化学式: C₁₉H₁₅ClN₂O₃
• 分子量: 354.793
• InChiKey: IMFKYXUMVFIFCL-SRZZPIQSSA-N

物化性质

• 熔点：
  298-300 °C
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  81.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide 、 二氯-二(苯基甲基)锡烷 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以75%的产率得到{[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dibenzyltin(IV)
  参考文献：
  名称：

  Synthesis, characterization and biological activity of diorganotin complexes with ONO terdentate Schiff base

  摘要：

  Diorganotin(IV) complexes with general formula R2SnL [H2L = (E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L1) and (E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L2); R = Me, Bu, Ph, Cy, Bz, o-ClBz and p-ClBz (1-14)] have been synthesized and characterized by IR, H-1, C-13 and Sn-119 NMR spectroscopic techniques and single crystal Xray diffractometry. The structure of the complexes, {[1-(5-bromo-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 1, {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 8 and {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dicyclohexyltin(IV), 11 reveals a five-coordinated, trigonal-bipyramidal geometry, whereby the trigonal plane of the complexes consists of the imine nitrogen atom and alkyl groups from the diorganotin moieties. The complexes are stabilized by a strong intramolecular hydrogen bonding between N(2) and O(3)-H(3). The Schiff bases and their corresponding diorganotin(IV) complexes have been evaluated against three human carcinoma cell lines, namely HT29 (human colon carcinoma cell line), SKOV-3 (human ovarian cancer cell line) and MCF7 (hormone-dependent breast carcinoma cell line), for their cytotoxic activities. The dimethyltin derivatives and dibutyltin derivatives of the Schiff base ligands display good cytotoxic activities against the tested cell lines. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.04.036
• 作为产物：
  描述：

  1-(3-氯苯基)-2-羟基乙酮 、 3-羟基-2-萘酸肼 以 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到(E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide
  参考文献：
  名称：

  Synthesis, characterization and biological activity of diorganotin complexes with ONO terdentate Schiff base

  摘要：

  Diorganotin(IV) complexes with general formula R2SnL [H2L = (E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L1) and (E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L2); R = Me, Bu, Ph, Cy, Bz, o-ClBz and p-ClBz (1-14)] have been synthesized and characterized by IR, H-1, C-13 and Sn-119 NMR spectroscopic techniques and single crystal Xray diffractometry. The structure of the complexes, {[1-(5-bromo-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 1, {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 8 and {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dicyclohexyltin(IV), 11 reveals a five-coordinated, trigonal-bipyramidal geometry, whereby the trigonal plane of the complexes consists of the imine nitrogen atom and alkyl groups from the diorganotin moieties. The complexes are stabilized by a strong intramolecular hydrogen bonding between N(2) and O(3)-H(3). The Schiff bases and their corresponding diorganotin(IV) complexes have been evaluated against three human carcinoma cell lines, namely HT29 (human colon carcinoma cell line), SKOV-3 (human ovarian cancer cell line) and MCF7 (hormone-dependent breast carcinoma cell line), for their cytotoxic activities. The dimethyltin derivatives and dibutyltin derivatives of the Schiff base ligands display good cytotoxic activities against the tested cell lines. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.04.036

文献信息

• EP2782643A1
  申请人：——

  公开号：EP2782643A1

  公开（公告）日：2014-10-01
• ANDROGEN RECEPTOR LIGANDS
  申请人：Lloyd David George

  公开号：US20140357682A1

  公开（公告）日：2014-12-04

  Non ligand binding pocket antagonists for the human androgen receptor. The androgen receptor (AR) is a member of the Nuclear Receptor (NR) family and its role is to modulate the biological effects of the endogenous androgens, testosterone (tes) and dihydrotestosterone (DHT). Synthetic androgens and anti-androgens have therapeutic value in the treatment of various androgen dependent conditions, from regulation of male fertility to prostate cancer. Current treatment of prostate cancer (PCa) typically involves administration of ‘classical’ antiandrogens, competitive inhibitors of natural AR ligands, DHT and tes, for the ligand binding pocket (LBP) in the C-terminal ligand binding domain (LBD) of the AR. However, prolonged LBP-targeting can often lead to androgen resistance and alternative therapies and therapeutic strategies are urgently required. Disclosed herein are a class of non-steroidal, small molecule AR antagonists which inhibit the transcriptional activity of the AR by non LBP-mediated modulation. The novel class reported demonstrates full (‘true’) antagonism in AR with low micromolar potency, high selectivity over both the Estrogen Receptors alpha and beta (ERα and ERβ) and the Glucocorticoid Receptor (GR) and only micromolar partial antagonism in the Progesterone Receptor (PR). Data provide compelling evidence for such non-LBP intervention as an alternative approach to classical PCa therapy. (Formula I).
• US9296716B2
  申请人：——

  公开号：US9296716B2

  公开（公告）日：2016-03-29
• [EN] ANDROGEN RECEPTOR LIGANDS<br/>[FR] LIGANDS DU RÉCEPTEUR DES ANDROGÈNES
  申请人：PROVOST FELLOWS & SCHOLARS COLLEGE OF THE HOLY UNDIVIDED TRINITY OF QUEEN ELIZABETH NEAR DUBLIN

  公开号：WO2013076275A1

  公开（公告）日：2013-05-30

  Non ligand binding pocket antagonists for the human androgen receptor. The androgen receptor (AR) is a member of the Nuclear Receptor (NR) family and its role is to modulate the biological effects of the endogenous androgens, testosterone (tes) and dihydrotestosterone (DHT). Synthetic androgens and anti-androgens have therapeutic value in the treatment of various androgen dependent conditions, from regulation of male fertility to prostate cancer. Current treatment of prostate cancer (PCa) typically involves administration of 'classical' antiandrogens, competitive inhibitors of natural AR ligands, DHT and tes, for the ligand binding pocket (LBP) in the C-terminal ligand binding domain (LBD) of the AR. However, prolonged LBP-targeting can often lead to androgen resistance and alternative therapies and therapeutic strategies are urgently required. Disclosed herein are a class of non-steroidal, small molecule AR antagonists which inhibit the transcriptional activity of the AR by non LBP-mediated modulation. The novel class reported demonstrates full ('true') antagonism in AR with low micromolar potency, high selectivity over both the Estrogen Receptors alpha and beta (ERα and ERβ) and the Glucocorticoid Receptor (GR) and only micromolar partial antagonism in the Progesterone Receptor (PR). Data provide compelling evidence for such non-LBP intervention as an alternative approach to classical PCa therapy. (Formula I).