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N-(3-((1R,2R)-2-aminocyclopropyl)phenyl)benzamide hydrochloride

中文名称
——
中文别名
——
英文名称
N-(3-((1R,2R)-2-aminocyclopropyl)phenyl)benzamide hydrochloride
英文别名
N-[3-[(1R,2R)-2-aminocyclopropyl]phenyl]benzamide;hydrochloride
N-(3-((1R,2R)-2-aminocyclopropyl)phenyl)benzamide hydrochloride化学式
CAS
——
化学式
C16H16N2O*ClH
mdl
——
分子量
288.777
InChiKey
JYVGWDQDLLYGPV-CTHHTMFSSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.18
  • 重原子数:
    20
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.19
  • 拓扑面积:
    55.1
  • 氢给体数:
    3
  • 氢受体数:
    2

反应信息

  • 作为产物:
    描述:
    3-硝基苯乙烯盐酸 、 tin(II) chloride dihdyrate 、 叠氮磷酸二苯酯四(3,5-二(三氟甲基)苯基)硼酸钠三乙胺 、 potassium hydroxide 作用下, 以 四氢呋喃1,4-二氧六环乙醇正己烷二氯甲烷乙酸乙酯 为溶剂, 反应 20.0h, 生成 N-(3-((1R,2R)-2-aminocyclopropyl)phenyl)benzamide hydrochloride
    参考文献:
    名称:
    Pure enantiomers of benzoylamino-tranylcypromine: LSD1 inhibition, gene modulation in human leukemia cells and effects on clonogenic potential of murine promyelocytic blasts
    摘要:
    The pure enantiomers of the N-(2-, 3-, and 4-(2-aminocyclopropyl)phenyl)benzamides hydrochlorides 11a-j were prepared and tested against LSD1 and MAO enzymes. The evaluation of the regioisomers 11a-j highlighted a net increase of the anti-LSD1 potency by shifting the benzamide moiety from ortho to meta and mainly to para position of tranylcypromine phenyl ring, independently from their trans or cis stereochemistry. In particular, the para-substituted 11a,b (trans) and 11g,h (cis) compounds displayed LSD1 and MAO-A inhibition at low nanomolar levels, while were less potent against MAO-B. The meta analogs 11c,d (trans) and 11i,j (cis) were in general less potent, but more efficient against MAO-A than against LSD1. In cellular assays, all the para and meta enantiomers were able to inhibit LSD1 by inducing Gfi-1b and ITGAM gene expression, with 11b,c and 11g-i giving the highest effects. Moreover, 11b and 11g,h strongly inhibited the clonogenic potential of murine promyelocytic blasts. (C) 2015 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2015.02.060
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文献信息

  • Pure enantiomers of benzoylamino-tranylcypromine: LSD1 inhibition, gene modulation in human leukemia cells and effects on clonogenic potential of murine promyelocytic blasts
    作者:Sergio Valente、Veronica Rodriguez、Ciro Mercurio、Paola Vianello、Bruna Saponara、Roberto Cirilli、Giuseppe Ciossani、Donatella Labella、Biagina Marrocco、Daria Monaldi、Giovanni Ruoppolo、Mats Tilset、Oronza A. Botrugno、Paola Dessanti、Saverio Minucci、Andrea Mattevi、Mario Varasi、Antonello Mai
    DOI:10.1016/j.ejmech.2015.02.060
    日期:2015.4
    The pure enantiomers of the N-(2-, 3-, and 4-(2-aminocyclopropyl)phenyl)benzamides hydrochlorides 11a-j were prepared and tested against LSD1 and MAO enzymes. The evaluation of the regioisomers 11a-j highlighted a net increase of the anti-LSD1 potency by shifting the benzamide moiety from ortho to meta and mainly to para position of tranylcypromine phenyl ring, independently from their trans or cis stereochemistry. In particular, the para-substituted 11a,b (trans) and 11g,h (cis) compounds displayed LSD1 and MAO-A inhibition at low nanomolar levels, while were less potent against MAO-B. The meta analogs 11c,d (trans) and 11i,j (cis) were in general less potent, but more efficient against MAO-A than against LSD1. In cellular assays, all the para and meta enantiomers were able to inhibit LSD1 by inducing Gfi-1b and ITGAM gene expression, with 11b,c and 11g-i giving the highest effects. Moreover, 11b and 11g,h strongly inhibited the clonogenic potential of murine promyelocytic blasts. (C) 2015 Elsevier Masson SAS. All rights reserved.
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同类化合物

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