N-((o-Nitrophenyl)sulfenyl)-4-(aminomethyl)benzoic acid | 244289-94-9

• 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: N-((o-Nitrophenyl)sulfenyl)-4-(aminomethyl)benzoic acid
• 英文别名: 4-((2-nitrophenylsulfonamido)methyl)benzoic acid；4-[[(2-Nitrophenyl)sulfonylamino]methyl]benzoic acid
• CAS: 244289-94-9
• 化学式: C₁₄H₁₂N₂O₆S
• 分子量: 336.325
• InChiKey: CQMAABJKWJDXNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((o-Nitrophenyl)sulfenyl)-4-(aminomethyl)benzoic acid 在 硫酸 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 苯硫酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 4-(((4-fluorobenzyl)(pyridin-3-ylmethyl)amino)methyl)-N-((S)-5-(3-(mesitylsulfonyl)guanidino)-1-(((R)-1-(naphthalen-1-yl)ethyl)amino)-1-oxopentan-2-yl)benzamide
  参考文献：
  名称：

  Pharmacophore-based small molecule CXCR4 ligands

  摘要：

  Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure-activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.032
• 作为产物：
  描述：

  4-氨甲基苯甲酸 、 邻硝基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-((o-Nitrophenyl)sulfenyl)-4-(aminomethyl)benzoic acid
  参考文献：
  名称：

  具有可变垫片的低分子量CXCR4配体

  摘要：

  设计并合成了基于已知前导化合物的低分子量CXCR4配体，其中包括14聚体肽T140，环状五肽FC131，模拟肽和二聚烯丙基胺。三种芳香族间隔基，1,4-苯二甲胺，萘-2-6-二基二甲胺和[1,1'-联苯] -4,4'-二基二甲胺被用于建立四个药效基团。作为药效基团，所有化合物中均存在2-吡啶基甲基和1-萘基甲基，还使用了1-丙基胍和1,1,3,3-四甲基-2-丙基胍中的几个芳族基团和阳离子基团。几种化合物显示出显着的CXCR4结合亲和力，而双（吡啶-2-基甲基）胺部分的锌（II）络合导致CXCR4结合亲和力显着增加。

  DOI：

  10.1002/cmdc.201200390

文献信息

• Cirauqui, Nuria; Ceras, Javier; Galiano, Silvia, Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 11, p. 585 - 591
  作者：Cirauqui, Nuria、Ceras, Javier、Galiano, Silvia、Perez-Silanes, Silvia、Juanenea, Laura、Rivera, Gildardo、Aldana, Ignacio、Monge, Antonio

  DOI：——

  日期：——
• Inhibitors of Glycinamide Ribonucleotide Formyltransferase as Potential Cytotoxic Agents. Synthesis of 5-Deaza-5,6,7,8-tetrahydrohomofolic Acid, 5-Deaza-5,6,7,8-tetrahydroisohomofolic Acid, and 10-Formyl-5-deaza-5,6,7,8-tetrahydroisohomofolic Acid
  作者：Edward C. Taylor、Cheol-min Yoon、James M. Hamby

  DOI：10.1021/jo00102a039

  日期：1994.11

  Syntheses of three new analogs of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF, Lometrexol)-5-deaza-5,6,7,8-tetrahydrohomofolic acid (11), 5-deaza-5,6,7,8-tetrahydroisohomofolic acid (16a), and 10-formyl-5-deaza-5,6,7,8-tetrahydroisohomofolic acid (16b)-are described.
• Low-Molecular-Weight CXCR4 Ligands with Variable Spacers
  作者：Tetsuo Narumi、Haruo Aikawa、Tomohiro Tanaka、Chie Hashimoto、Nami Ohashi、Wataru Nomura、Takuya Kobayakawa、Hikaru Takano、Yuki Hirota、Tsutomu Murakami、Naoki Yamamoto、Hirokazu Tamamura

  DOI：10.1002/cmdc.201200390

  日期：2013.1

  Low‐molecular‐weight CXCR4 ligands based on known lead compounds including the 14‐mer peptide T140, the cyclic pentapeptide FC131, peptide mimetics, and dipicolylamine‐containing compounds were designed and synthesized. Three types of aromatic spacers, 1,4‐phenylenedimethanamine, naphthalene‐2,6‐diyldimethanamine, and [1,1′‐biphenyl]‐4,4′‐diyldimethanamine, were used to build four pharmacophore groups

  设计并合成了基于已知前导化合物的低分子量CXCR4配体，其中包括14聚体肽T140，环状五肽FC131，模拟肽和二聚烯丙基胺。三种芳香族间隔基，1,4-苯二甲胺，萘-2-6-二基二甲胺和[1,1'-联苯] -4,4'-二基二甲胺被用于建立四个药效基团。作为药效基团，所有化合物中均存在2-吡啶基甲基和1-萘基甲基，还使用了1-丙基胍和1,1,3,3-四甲基-2-丙基胍中的几个芳族基团和阳离子基团。几种化合物显示出显着的CXCR4结合亲和力，而双（吡啶-2-基甲基）胺部分的锌（II）络合导致CXCR4结合亲和力显着增加。
• Pharmacophore-based small molecule CXCR4 ligands
  作者：Tetsuo Narumi、Tomohiro Tanaka、Chie Hashimoto、Wataru Nomura、Haruo Aikawa、Akira Sohma、Kyoko Itotani、Miyako Kawamata、Tsutomu Murakami、Naoki Yamamoto、Hirokazu Tamamura

  DOI：10.1016/j.bmcl.2012.04.032

  日期：2012.6

  Low molecular weight CXCR4 ligands were developed based on the peptide T140, which has previously been identified as a potent CXCR4 antagonist. Some compounds with naphthyl, fluorobenzyl and pyridyl moieties as pharmacophore groups in the molecule showed significant CXCR4-binding activity and anti-HIV activity. Structure-activity relationships were studied and characteristics of each of these three moieties necessary for CXCR4 binding were defined. In this way, CXCR4 ligands with two types of recognition modes for CXCR4 have been found. (C) 2012 Elsevier Ltd. All rights reserved.