2-[[(1,1-二甲基乙氧基)羰基]氨基]-5-甲氧基苯甲酸 | 262614-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[[(1,1-二甲基乙氧基)羰基]氨基]-5-甲氧基苯甲酸
• 中文别名: 2-N-Boc-氨基-5-甲氧基苯甲酸；2-N-BOC-氨基-5-甲氧基苯甲酸
• 英文名称: 2-(tert-butoxycarbonylamino)-5-methoxybenzoic acid
• 英文别名: 2-N-Boc-Amino-5-methoxybenzoic acid；5-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]benzoic acid
• CAS: 262614-64-2
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: JBXGOBGRVPAQEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.7±32.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-[[(1,1-二甲基乙氧基)羰基]氨基]-5-甲氧基苯甲酸 在 4-二甲氨基吡啶 、 1,1-二氯甲醚 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 27.0h， 生成 (S)-4-(2-(2-amino-5-methoxybenzoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide
  参考文献：
  名称：

  Novel Class of Benzoic Acid Ester Derivatives as Potent PDE4 Inhibitors for Inhaled Administration in the Treatment of Respiratory Diseases

  摘要：

  The first steps in the selection process of a new anti-inflammatory drug for the inhaled treatment of asthma and chronic obstructive pulmonary disease are herein described. A series of novel ester derivatives of 1-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3,5-di-chloropyriclin-4-yl) ethanol have been synthesized and evaluated for inhibitory activity toward cAMP-specific phosphodiesterase-4 (PDE4). In particular, esters of variously substituted benzoic acids were extensively explored, and structural modification of the alcoholic and benzoic moieties were performed to maximize the inhibitory potency. Several compounds with high activity in cell-free and cell-based assays were obtained. Through the evaluation of opportune in vitro ADME properties, a potential candidate suitable for inhaled administration in respiratory diseases was identified and tested in an in vivo model of pulmonary inflammation, proving its efficacy.

  DOI：

  10.1021/jm401549m
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-氨基-5-甲氧基苯甲酸 在 吡啶 作用下， 反应 2.5h， 以78%的产率得到2-[[(1,1-二甲基乙氧基)羰基]氨基]-5-甲氧基苯甲酸
  参考文献：
  名称：

  通过基于片段的筛选发现首个结核分枝杆菌MabA（FabG1）抑制剂。

  摘要：

  结核分枝杆菌（M.tb）是结核病的病原体，仍然是全球单一传染病致死的主要原因。耐药性结核分枝杆菌的出现菌株强调需要药物作用于新靶标。分枝杆菌酸是很长的链脂肪酸，在分枝杆菌细胞壁的结构和渗透性中起着至关重要的作用。它们的生物合成涉及两个脂肪酸合酶（FAS）系统。在FAS-II周期的四种酶（MabA，HadAB / BC，InhA和KasA / B）中，MabA（FabG1）仍然是唯一尚未报道特异性抑制剂的酶。新的基于LC-MS / MS的酶促测定方法的开发，可以筛选1280个片段文库，并导致发现了第一个抑制MabA活性的小分子。将邻氨基苯甲酸系列的片段优化为更有效的抑制剂，并通过19 F配体观察的NMR实验证实了它们与MabA的结合。

  DOI：

  10.1016/j.ejmech.2020.112440

文献信息

• Escaping from Flatland: Antimalarial Activity of sp³-Rich Bridged Pyrrolidine Derivatives
  作者：Brian Cox、James Duffy、Victor Zdorichenko、Corentin Bellanger、Jessica Hurcum、Benoît Laleu、Kevin I. Booker-Milburn、Luke D. Elliott、Michael Robertson-Ralph、Christopher J. Swain、Stephen J. Bishop、Irene Hallyburton、Mark Anderson

  DOI：10.1021/acsmedchemlett.0c00486

  日期：2020.12.10

  We utilized synthetic photochemistry to generate novel sp3-rich scaffolds and report the design, synthesis, and biological testing of a diverse series of amides based on the 1-(amino-methyl)-2-benzyl-2-aza-bicyclo[2.1.1]hexane scaffold. Preliminary antimalarial screening of the library provided promising compounds with activity in the 1–5 μM range with an enhanced hit rate. Further evaluation (solubility

  我们利用合成光化学生成了新型富含sp 3 的支架，并报告了基于 1-（氨基-甲基）-2-苄基-2-氮杂-双环 [2.1 .1]己烷支架。该文库的初步抗疟筛选提供了有希望的化合物，其活性范围为 1–5 μM，并具有更高的命中率。所选化合物 ( 9 ) 的进一步评估（溶解度、药物代谢和药代动力学 (DMPK) 和毒性）表明，该系列代表了进一步优化的绝佳机会，该框架为添加独特的矢量定位的额外功能提供了多种机会。
• Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines
  作者：Zhigang Xu、Justin Dietrich、Arthur Y. Shaw、Christopher Hulme

  DOI：10.1016/j.tetlet.2010.06.116

  日期：2010.8

  A two-step solution phase synthesis employing a double UDC (Ugi/Deprotect/Cyclize) strategy has been utilized to obtain fused 6,7,6,6-quinoxalinone-benzodiazepines and 6,7,7,6-bis-benzodiazepines. Optimization of the methodology to produce these tetracyclic scaffolds was enabled by microwave irradiation, incorporation of trifluoroethanol as solvent, and the use of the convertible isocyanide, 4-tert-butyl

  采用双 UDC（Ugi/脱保护/环化）策略的两步液相合成已被用于获得融合的 6,7,6,6-喹喔啉酮-苯二氮卓类和 6,7,7,6-双-苯二氮卓类。通过微波辐射、加入三氟乙醇作为溶剂以及使用可转化的异氰化物 4-叔丁基环己烯-1-基异氰化物来优化生产这些四环支架的方法。
• New derivatives of amidines, their preparation, their use as medicaments and the pharmaceutical compositions containing them
  申请人：Auvin Serge

  公开号：US20050261269A1

  公开（公告）日：2005-11-24

  Novel derivatives of amidines of formula wherein the substituents are defined as in the specification which are useful for inhibiting activity on NO-synthase enzymes producing nitrogen mono oxide and/or trapping the reactive oxygen species (ROS) making them useful for treating various diseases.

  该项发明涉及公式中所定义的取代基的新型氨基甲酸酰胺衍生物，其对产生一氧化氮的NO合酶酶活性具有抑制作用，并且对于捕获反应性氧化物种（ROS）也具有作用，因此对于治疗各种疾病是有用的。
• Synthesis of a quinolone library from ynones
  作者：Timothy R. Ward、Brandon J. Turunen、Torsten Haack、Benjamin Neuenswander、William Shadrick、Gunda I. Georg

  DOI：10.1016/j.tetlet.2009.09.024

  日期：2009.11

  A library of 72 quinolones was synthesized from substituted anthranilic acids, using ynone intermediates. These masked beta-dicarbonyl synthons allowed cyclization under milder conditions than previously reported quinolone syntheses. (C) 2009 Elsevier Ltd. All rights reserved
• An efficient solution phase synthesis of triazadibenzoazulenones: ‘designer isonitrile free’ methodology enabled by microwaves
  作者：Christopher Hulme、Shashi Chappeta、Chris Griffith、Yeon-Sun Lee、Justin Dietrich

  DOI：10.1016/j.tetlet.2009.02.099

  日期：2009.4

  A novel two-step solution phase protocol for the synthesis of arrays of triazadibenzoazulenones is reported. The methodology employs the Ugi reaction to assemble desired diversity and acid treatment enables two tandem ring closing transformations. The order of ring closure is shown to be key for optimal conversion to the desired tetra-cyclic product and initially proceeds through a benzimidazole intermediate, followed by second ring closure to give the desired fused benzodiazepine. The two-step protocol is further facilitated by microwave irradiation. Prudent selection of the isonitrile reagent enables the correct order of ring forming events. As such the methodology represents the first example of a post-condensation Ugi modification that employs two internal amino nucleophiles. (C) 2009 Elsevier Ltd. All rights reserved.