N-邻苯二甲酰组氨酸 | 14997-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-邻苯二甲酰组氨酸
• 英文名称: N-phthaloyl histidine
• 英文别名: N^α,N^α-phthaloyl-histidine；N^α-Phthaloyl-L-histidin；N-Phthaloyl-L-histidin；N-Phthalyl-L-histidin；(2S)-2-(1,3-dioxoisoindol-2-yl)-3-(1H-imidazol-5-yl)propanoic acid
• CAS: 14997-56-9
• 化学式: C₁₄H₁₁N₃O₄
• mdl: MFCD00412015
• 分子量: 285.259
• InChiKey: CTUUVOUXZNQMSU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-邻苯二甲酰组氨酸 以 丙酮 为溶剂， 反应 3.0h， 以29.8%的产率得到2-(2-(1H-imidazol-4-yl)ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Sato, Yasuhiko; Nakai, Hideo; Mizoguchi, Tomishige, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 4, p. 1263 - 1270

  摘要：

  DOI：
• 作为产物：
  描述：

  N^α-(2-carboxy-benzoyl)-L-histidine 在 phosphorus pentoxide 作用下， 生成 N-邻苯二甲酰组氨酸
  参考文献：
  名称：

  Helferich; Boeshagen, Chemische Berichte, 1959, vol. 92, p. 2813,2826

  摘要：

  DOI：

文献信息

• Photoinduced electron-transfer chemistry of the bielectrophoric <i>N</i>-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan
  作者：Axel G Griesbeck、Jörg Neudörfl、Alan de Kiff

  DOI：10.3762/bjoc.7.60

  日期：——

  tyrosine, histidine and tryptophan 8-10 was studied with respect to photoinduced electron-transfer (PET) induced decarboxylation and Norrish II bond cleavage. Whereas exclusive photodecarboxylation of the tyrosine substrate 8 was observed, the histidine compound 9 resulted in a mixture of histamine and preferential Norrish cleavage. The tryptophan derivative 10 is photochemically inert and shows preferential

  研究了富含电子的氨基酸酪氨酸、组氨酸和色氨酸 8-10 的邻苯二甲酰亚胺衍生物的光化学，涉及光诱导电子转移 (PET) 诱导的脱羧和 Norrish II 键裂解。虽然观察到酪氨酸底物 8 的排他性光脱羧，但组氨酸化合物 9 导致组胺和优先 Norrish 裂解的混合物。色氨酸衍生物 10 是光化学惰性的，只有在分子间 PET 诱导时才显示出优先脱羧作用。
• [EN] INHIBITORS OF ATP SYNTHASE - COSMETIC AND THERAPEUTIC USES<br/>[FR] INHIBITEURS D'UTILISATIONS COSMÉTIQUES ET THÉRAPEUTIQUES D'ATP SYNTHASE
  申请人：FORREST MICHAEL DAVID

  公开号：WO2022157548A1

  公开（公告）日：2022-07-28

  With supporting experimental data, this disclosure teaches that IF1 protein activity is a molecular determinant of lifespan, therein explaining why different species have different maximal lifespans, and it teaches a IF1 protein/fragment (or sequence variant thereof), or a fusion protein thereof, optionally a fusion protein comprising a Cell Penetrating Peptide (CPP) sequence, as an agent to slow/delay/reduce aging in a subject, optionally as a component of a cosmetic, optionally to treat an age-correlated disease/disorder. Moreover it teaches other inhibitors of F1F0 ATP hydrolysis, including small molecules, of a number of different scaffolds, for this purpose. Furthermore, with supporting experimental data, it teaches that compounds that slow the ATP-hydrolysing mode of ATP synthase are useful for treating various diseases and disorders, including cancer, particularly cancers that utilise the Warburg effect.

  本公开教导了IF1蛋白活性是寿命的分子决定因素，通过支持实验数据解释了不同物种具有不同最大寿命的原因。本公开教导了使用IF1蛋白/片段（或其序列变体）或其融合蛋白作为减缓/延迟/减少受试者衰老的药剂，可选作为化妆品组分，可选用于治疗与年龄相关的疾病/失调。此外，本公开还教导了其他F1F0 ATP水解抑制剂，包括多种不同支架的小分子，用于此目的。此外，通过支持实验数据，本公开还教导了减缓ATP合成酶的ATP水解模式的化合物对于治疗各种疾病和失调的有用性，包括癌症，特别是利用Warburg效应的癌症。
• Novel tricyclic aminoacetyl and sulfonamide inhibitors of Ras farnesyl protein transferase
  作者：F.George Njoroge、Bancha Vibulbhan、Carmen S. Alvarez、W.Robert Bishop、Joanne Petrin、Ronald J. Doll、V. Girijavallabhan、Ashit K. Ganguly

  DOI：10.1016/s0960-894x(96)00558-6

  日期：1996.12

  Novel tricyclic FPT inhibitors with submicromolar FPT activity are described. Greatly enhanced FPT activity is realized with phthaloyl derivatized amino compound 2k, which showed FPT inhibitory activity of IC50 = 0.66 mu M. Sulfonamides 5g and 50 were also found to be potent FPT inhibitor. SAR resulting from a variety of tricyclic amino acids and sulfonamide derivatives is discussed. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis and Evaluation of Analogues of <i>N</i>-Phthaloyl-<scp>l</scp>-tryptophan (RG108) as Inhibitors of DNA Methyltransferase 1
  作者：Saâdia Asgatay、Christine Champion、Gaël Marloie、Thierry Drujon、Catherine Senamaud-Beaufort、Alexandre Ceccaldi、Alexandre Erdmann、Arumugam Rajavelu、Philippe Schambel、Albert Jeltsch、Olivier Lequin、Philippe Karoyan、Paola B. Arimondo、Dominique Guianvarc’h

  DOI：10.1021/jm401419p

  日期：2014.1.23

  DNA methyltransferases (DNMT) are promising drug targets in cancer provided that new, more specific, and chemically stable inhibitors are discovered. Among the non-nucleoside DNMT inhibitors, N-phthaloyl-L-tryptophan 1 (RG108) was first identified as inhibitor of DNMT1. Here, 1 analogues were synthesized to understand its interaction with DNMT. The indole, carboxylate, and phthalimide moieties were modified. Homologated and conformationally constrained analogues were prepared. The latter were synthesized from prolinohomotryptophan derivatives through a methodology based amino-zinc-ene-enolate cyclization. All compounds were tested for their ability to inhibit DNMT1 in vitro. Among them, constrained compounds 16-18 and NPys derivatives 10-11 were found to be at least 10-fold more potent than the reference compound. The cytotoxicity on the tumor, DU145 cell line of the most potent inhibitors was correlated to their inhibitory potency. Finally, docking studies were conducted in order to understand their binding mode. This study provides insights for the design of the next-generation of DNMT inhibitors.
• Auterhoff; Hansen, Pharmazie, 1970, vol. 25, # 5, p. 336 - 340
  作者：Auterhoff、Hansen

  DOI：——

  日期：——