trans-2-(m-nitrophenyl)cyclopropanecarboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-2-(m-nitrophenyl)cyclopropanecarboxylic acid
• 英文别名: trans 2-(3-nitrophenyl)cyclopropylcarboxylic acid；(+/-)-trans-2-(3-nitro-phenyl)-cyclopropanecarboxylic acid；(+/-)-trans-2-(3-Nitro-phenyl)-cyclopropancarbonsaeure；(1S,2S)-2-(3-nitrophenyl)cyclopropane-1-carboxylic acid
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: MZCREXORTQFYPP-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-2-(m-nitrophenyl)cyclopropanecarboxylic acid 在 盐酸 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 trans-2-(3-Nitrophenyl)cyclopropanamine
  参考文献：
  名称：

  探索A3腺苷受体结合位点的远端区域：在空间上受约束的N6-（2-苯乙基）腺苷衍生物作为有效的配体。

  摘要：

  我们合成了N（6）-（1S，2R）-（2-苯基-1-环丙基）腺苷的苯环取代类似物，其与人A（3）AR的结合力强，Ki值为0.63 nM。测量了这些结构变化对人和大鼠腺苷受体的亲和力以及对hA（3）AR的内在功效的影响。3-硝基苯基类似物色谱分离成纯的非对映异构体，在A（3）AR结合中表现出10倍的立体选择性，有利于1S，2R异构体。分子模型在苯基部分周围的假定的A（3）AR结合位点中定义了疏水区（Phe168）。杂芳族基团（3-噻吩基）可以取代苯基部分，并保留A（3）AR结合的高亲和力。包括其他相关的N（6）取代腺苷衍生物进行比较。尽管N（6）-（2-苯基-1-环丙基）衍生物是完全的A（3）AR激动剂，但其他几种衍生物的功效也大大降低。N（6）-环丙基腺苷是一种A（3）AR拮抗剂，在环丙基部分的2位添加一个或两个苯环可恢复功效。N（6）-（2,2-二苯基乙基）腺苷是一种A（3）AR拮抗剂，

  DOI：

  10.1016/j.bmc.2004.02.037
• 作为产物：
  描述：

  3-硝基苯乙烯 在 copper(l) chloride 、 potassium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 trans-2-(m-nitrophenyl)cyclopropanecarboxylic acid
  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

文献信息

• Conjugative Transmission in Cyclopropane Systems
  作者：Edward N. Trachtenberg、George Odian

  DOI：10.1021/ja01548a051

  日期：1958.8
• Korp, James D.; Bernal, Ivan; Fuchs,, Richard, Canadian Journal of Chemistry, 1983, vol. 61, p. 50 - 56
  作者：Korp, James D.、Bernal, Ivan、Fuchs,, Richard

  DOI：——

  日期：——
• 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.
• Exploring distal regions of the A3 adenosine receptor binding site: sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands
  作者：Susanna Tchilibon、Soo-Kyung Kim、Zhan-Guo Gao、Brian A Harris、Joshua B Blaustein、Ariel S Gross、Heng T Duong、Neli Melman、Kenneth A Jacobson

  DOI：10.1016/j.bmc.2004.02.037

  日期：2004.5

  putative A(3)AR binding site around the phenyl moiety. A heteroaromatic group (3-thienyl) could substitute for the phenyl moiety with retention of high affinity of A(3)AR binding. Other related N(6)-substituted adenosine derivatives were included for comparison. Although the N(6)-(2-phenyl-1-cyclopropyl) derivatives were full A(3)AR agonists, several other derivatives had greatly reduced efficacy. N(6)

  我们合成了N（6）-（1S，2R）-（2-苯基-1-环丙基）腺苷的苯环取代类似物，其与人A（3）AR的结合力强，Ki值为0.63 nM。测量了这些结构变化对人和大鼠腺苷受体的亲和力以及对hA（3）AR的内在功效的影响。3-硝基苯基类似物色谱分离成纯的非对映异构体，在A（3）AR结合中表现出10倍的立体选择性，有利于1S，2R异构体。分子模型在苯基部分周围的假定的A（3）AR结合位点中定义了疏水区（Phe168）。杂芳族基团（3-噻吩基）可以取代苯基部分，并保留A（3）AR结合的高亲和力。包括其他相关的N（6）取代腺苷衍生物进行比较。尽管N（6）-（2-苯基-1-环丙基）衍生物是完全的A（3）AR激动剂，但其他几种衍生物的功效也大大降低。N（6）-环丙基腺苷是一种A（3）AR拮抗剂，在环丙基部分的2位添加一个或两个苯环可恢复功效。N（6）-（2,2-二苯基乙基）腺苷是一种A（3）AR拮抗剂，