2-萘基甲基异氰酸酯 | 191855-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-萘基甲基异氰酸酯
• 英文名称: 2-naphthylmethylisocyanate
• 英文别名: 2-(isocyanatomethyl)naphthalene
• CAS: 191855-57-9
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: CITIVFHZQRITJO-UHFFFAOYSA-N

物化性质

• 沸点：
  316.9±21.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-萘基甲基异氰酸酯 在 4-二甲氨基吡啶 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-{3,3-Diethyl-1-[(naphthalen-2-ylmethyl)-carbamoyl]-4-oxo-azetidin-2-yloxy}-benzoic acid
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  β-naphthylacetyl azide 反应 0.5h， 生成 2-萘基甲基异氰酸酯
  参考文献：
  名称：

  Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties

  摘要：

  Lactenediynes are compounds characterized by the fusion of a beta-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.022

文献信息

• Beta lactam compounds and their use as inhibitors of tryptase
  申请人：Bristol-Myers Squibb Co.

  公开号：US06335324B1

  公开（公告）日：2002-01-01

  Compounds of the formulas: are disclosed. These compounds inhibit tryptase as well as other enzyme systems or are selective tryptase inhibitors and are useful as antiinflammatory agents particularly in the treatment of chronic asthma.

  这些化合物的结构式已被披露。这些化合物抑制色胺酸蛋白酶以及其他酶系统，或者是选择性色胺酸蛋白酶抑制剂，并且在特别是治疗慢性哮喘方面作为抗炎药物是有用的。
• [EN] AMIDINO AND GUANIDINO AZETIDINONE TRYPTASE INHIBITORS<br/>[FR] INHIBITEURS D'AMIDINO ET GUANIDINO AZETIDONONE TRYPTASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999067215A1

  公开（公告）日：1999-12-29

  (EN) Compounds of formulae (I), (II), (III).(FR) L'invention concerne des composés correspondant aux formules (I), (II) et (III).

  这是中文翻译： (EN) Compounds of formulae (I), (II), (III). 对应于公式(I)，(II)，(III)的化合物。 (FR) L'invention concerne des composés correspondant aux formules (I), (II) et (III). 该发明涉及对应于公式(I)，(II)，(III)的化合物。
• Assessment of the structure-activity relationship and antileukemic activity of diacylpyramide compounds as human ClpP agonists
  作者：Ranran Zhang、Pengyu Wang、Bingyan Wei、Liang Chen、Xiaomin Song、Yihui Pan、Jiahui Li、Jianhua Gan、Tao Zhang、Cai-Guang Yang

  DOI：10.1016/j.ejmech.2023.115577

  日期：2023.10

  (ClpP) is required for the regulatory hydrolysis of mitochondrial proteins. Allosteric ClpP agonists dysfunctionally activate mitochondrial ClpP in antileukemic therapies. We previously developed ZG111, a potent ClpP agonist derived from ICG-001, inhibits the proliferation of pancreatic ductal adenocarcinoma cell lines in vitro and in vivo by degrading respiratory chain complex proteins. Herein, we studied

  线粒体蛋白的调节性水解需要人酪蛋白分解酶 P (ClpP) 。在抗白血病治疗中，变构 ClpP 激动剂会功能失调地激活线粒体 ClpP 。我们之前开发了ZG111 ，一种源自ICG-001的有效 ClpP 激动剂，通过降解呼吸链复合蛋白在体外和体内抑制胰腺导管腺癌细胞系的增殖。在此，我们研究了ICG-001类似物作为抗白血病药物的构效关系。与ZG111的稳定作用相比，化合物ZG36对急性髓系白血病（AML）细胞系中ClpP的热稳定性表现出改善的稳定作用，表明ZG36和ClpP之间的直接结合。事实上，解析的ZG36 /ClpP 结构复合物揭示了ZG36在 ClpP 结合过程中的作用模式。化合物ZG36非选择性降解呼吸链复合物并减少线粒体 DNA，最终导致线粒体功能崩溃和白血病细胞死亡。最后， ZG36治疗可抑制体外3-D 细胞生长，并抑制异种移植小鼠模型中 AML 细胞的肿瘤发生。 总的来说，我们开发了一种新型人类
• [DE] AMINOSÄUREDERIVATE, DIESE VERBINDUNGEN ENTHALTENDE ARZNEIMITTEL UND VERFAHREN ZU IHRER HERSTELLUNG<br/>[EN] AMINO ACID DERIVATIVES, MEDICAMENTS CONTAINING SAID COMPOUNDS AND METHODS OF PRODUCING SAID COMPOUNDS<br/>[FR] DERIVES D'ACIDES AMINES, MEDICAMENTS CONTENANT CES COMPOSES ET PROCEDE DE PRODUCTION CORRESPONDANT
  申请人：DR. KARL THOMAE GMBH

  公开号：WO1997019914A1

  公开（公告）日：1997-06-05

  (DE) Die Erfindung betrifft neue Aminosäurederivate der allgemeinen Formel (I), in der R, U, V, Y, n, m und R1 bis R3 wie im Anspruch 1 definiert sind, deren Tautomere, deren Diastereomere, deren Enantiomere, deren Gemische und deren Salze, insbesondere deren physiologisch verträgliche Salze mit anorganischen oder organischen Säuren oder Basen, welche wertvolle pharmakologische Eigenschaften aufweisen, insbesondere selektive NPY-antagonistische Eigenschaften, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung.(EN) The invention relates to novel amino acid derivatives of general formula (I), in which R, U, V, Y, n, m and R1-R3 have the definitions shown in claim 1, and to their tautomers, diastereomers, enantiomers, mixtures and salts, in particular their physiologically tolerable salts with inorganic or organic acids or bases, which have useful pharmacological properties, in particular selective NPY-antagonistic properties. Also disclosed are medicaments containing these compounds, their use and methods of producing them.(FR) L'invention concerne de nouveaux dérivés d'acides aminés de la formule (I) où R, U, V, Y, n, m et R1 à R3 ont la signification donnée dans la revendication 1. L'invention concerne également leurs tautomères, leurs diastéréomères, leurs énantiomères, leurs mélanges et leurs sels, notamment leurs sels physiologiquement tolérables avec des acides et bases inorganiques ou organiques qui présentent de précieuses propriétés pharmacologiques, notamment des propriétés d'antagonisme de NPY. L'invention concerne par ailleurs des médicaments contenant ces composés, leur utilisation et leur procédé de production.

  这项发明涉及新的氨基酸衍生物，其一般化学式为(I)，其中R、U、V、Y、n、m及R1至R3的定义如第1条所述。这些化合物的本体、官能团异构体（tautomers）、构型异构体（diastereomers）、官能团镜像异构体（enantiomers）、混合物及其盐。特别是与无机或有机酸、碱的生理相容盐。本发明还涉及含该化合物的医药品及其用法和制备方法。
• Synthesis and evaluation of ureido and vinylureidopenicillins as inhibitors of intraruminal lactic acid production
  作者：Robin D. Clark、Joan M. Caroon、Ian T. Harrison、Arthur F. Kluge、Stefan H. Unger、Howard R. Spires、Thomas R. Mathews

  DOI：10.1021/jm00142a024

  日期：1981.10

  A series of 14 vinylureidopenicillins and a series of 9 ureidopenicillins were prepared by reaction of 6-aminopenicillanic acid with vinyl isocyanates and isocyanates. These compounds were evaluated for their potential to protect ruminants against lactic acidosis. The compounds were tested for inhibition of in vitro ruminal lactic and propionic acid production, and six compounds inhibited lactic acid production to less than 10% of control at doses of 0.31 microgram/mL or lower, whereas they did not inhibit propionic acid production at doses greater than 10 micrograms/mL. The most active compounds also were screened for general antibacterial activity and were found to be weakly active against Gram-positive bacteria. The structure--activity relationships are discussed for both series. Triethylammonium 6-[3[2-(4-tert-butylphenyl)vinyl]ureido]penicillanate (4) was chosen for evaluation as an inhibitor of intraruminal lactic acidosis in vivo.