benzyl 2-hydroxy-5-nitrobenzoate | 155388-71-9

• 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: benzyl 2-hydroxy-5-nitrobenzoate
• CAS: 155388-71-9
• 化学式: C₁₄H₁₁NO₅
• 分子量: 273.245
• InChiKey: DNKITKPTEJNJOU-UHFFFAOYSA-N

物化性质

• 熔点：
  83.5-85.5 °C
• 沸点：
  440.9±35.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-hydroxy-5-nitrobenzoate 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 potassium acetate 、 三乙酰氧基硼氢化钠 、 铁粉 、 溶剂黄146 、 三苯基膦 、 联硼酸频那醇酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 25.5h， 生成 2'-benzyl 2-tert-butyl 4-methyl 4'-(cyclohexylamino)biphenyl-2,2',4-tricarboxylate
  参考文献：
  名称：

  含有非am P1配体的选择性和口服TF / FVIIa复合抑制剂的设计，合成和生物学活性。

  摘要：

  我们发现了新型的选择性和口服可用的非amTF / FVIIa复合抑制剂21e，4-（{[（（S）-（氨基羰基）-3-甲基丁基]氨基}羰基）-2'-（{[ ）苯基]氨基}羰基）-4'-（甲基氨基）联苯-2-羧酸。通过转化异丁基部分和将烷基氨基基团引入到先前报道的化合物2a和2b的中心苯环的4'-位来合成衍生物。一些化合物显示出增加的体外抗TF / FVIIa和PT延长活性。其中，化合物21e在小鼠口服后达到并维持高达2h的微摩尔血浆浓度水平。此外，即使在食蟹猴中，即使在最高剂量水平下，化合物21e也不会延长出血时间，而在该剂量下PT延长了3.7倍。

  DOI：

  10.1016/j.bmc.2006.09.071
• 作为产物：
  描述：

  邻羟基苯乙酸 在 氯化亚砜 、 硝酸 作用下， 反应 8.0h， 生成 benzyl 2-hydroxy-5-nitrobenzoate
  参考文献：
  名称：

  Structure-Activity Relationships in a Series of 5-[(2,5-Dihydroxybenzyl)amino]salicylate Inhibitors of EGF-Receptor-Associated Tyrosine Kinase: Importance of Additional Hydrophobic Aromatic Interactions

  摘要：

  Potent inhibitors of EGF-dependent protein tyrosine kinase (PTK) activity were synthesized in a series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Several of these compounds inhibited EGF-dependent DNA synthesis in ER 22 cells with IC50 < 1 muM. In this series of PTK inhibitors, the role of the salicylate moiety as a potential divalent ion chelator was tested and found to be nonessential in all cases. The length and ramification of the substituting carboxyl group were investigated to improve cellular bioavailability, and this analysis provided compounds with increased inhibitory effect on EGF-induced DNA synthesis. Salicylates esterified with long hydrophobic chains were shown to be noncompetitive inhibitors of ATP, in contrast to the free acid and methyl salicylate. Moreover, all the tested inhibitors were shown to be noncompetitive inhibitors of the peptide substrate. Structure-activity relationships allowed us to suspect a hydrophobic pocket in the tyrosine kinase domain, preferentially interacting with aromatic rings. Finally, the selectivity of the best inhibitors was tested against other kinases, and they were found to be selective for tyrosine kinase. They were also shown to be good inhibitors of EGF-receptor autophosphorylation.

  DOI：

  10.1021/jm00032a020

文献信息

• One‐Pot Synthetic Procedure for2,2′‐Disubstituted Biaryls via the Suzuki Coupling Reaction of Aryl Triflates in a Biphasic Solvent System
  作者：Masanori Miura、Takanori Koike、Tsukasa Ishihara、Fukushi Hirayama、Shuichi Sakamoto、Minoru Okada、Mitsuaki Ohta、Shin‐ichi Tsukamoto

  DOI：10.1080/00397910600948088

  日期：2006.12

  Abstract A one‐pot synthetic procedure for 2,2′‐disubstituted biaryls was developed via a Suzuki cross‐coupling reaction of aryl triflates in a biphasic solvent system. The effects of various bases and solvents were investigated. Results showed that the Na2CO3–toluene/H2O combination gave the highest yields.

  摘要 通过芳基三氟甲磺酸酯在双相溶剂体系中的 Suzuki 交叉偶联反应开发了 2,2'-二取代联芳基的一锅法合成方法。研究了各种碱和溶剂的影响。结果表明，Na2CO3-甲苯/H2O 组合的产量最高。
• 3-O-Demethyl derivatives of sannamycin C and antibiotic AX-127B-1
  申请人：ABBOTT LABORATORIES

  公开号：EP0035337A1

  公开（公告）日：1981-09-09

  3-O-demethylsannamycin C, 3-O-demethyl-antibiotic AX-127B-1 and their 4-N-and 2'-N-acyl and alkyl derivatives represented by the formula wherein: R is hydrogen or methyl, R2 and R3 are the same or different members of the group consisting of hydrogen, acyl, aminoacyl, diaminoacyl, N-loweralkylaminoacyl, N,N-dilower- alkylaminoacyl, hydroxy-substituted aminoacyl, loweralkyl, aminoloweralkyl, diaminoloweralkyl, hydroxyloweralkyl, N-low- eralkylaminoloweralkyl, N,N-diloweralkylaminoloweralkyl, N-loweralkylaminohydroxyloweralkyl and N,N-diloweralkylami- no-hydroxyloweralkyl; R4 and R5 are hydrogen or amino with the limitation that one of either R4 or R5 must be hydrogen; R6 and R7 are selected from the group consisting of hydrogen, hydroxy, amino and chloro with the limitation that one of either R6 or R7 must be hydrogen; R8 and R9 or hydrogen or hydroxy with the limitation that one of either R8 or R9 must be hydrogen are provided. The compounds are broad spectrum antibiotics and anti-bacterial agents.

  3-O-去甲基山奈霉素 C、3-O-去甲基抗生素 AX-127B-1 及其 4-N-酰基和 2'-N-酰基及烷基衍生物，其代表式为 其中R是氢或甲基，R2和R3是由氢、酰基、氨基酰基、二氨基酰基、N-低级烷基氨基酰基、N,N-二低级烷基氨基酰基、羟基取代的氨基酰基组成的组中相同或不同的成员、下烷基、氨基下烷基、二氨基下烷基、羟基下烷基、N-低烷基氨基下烷基、N,N-二低烷基氨基下烷基、N-低烷基氨基羟基下烷基和 N,N-二低烷基氨基-无羟基下烷基；R4和R5为氢或氨基，但R4或R5中必须有一个是氢；R6和R7选自由氢、羟基、氨基和氯组成的组，但R6或R7中必须有一个是氢；R8和R9为氢或羟基，但R8或R9中必须有一个是氢。这些化合物是广谱抗生素和抗菌剂。
• Active agents and methods of their use for the treatment of metabolic disorders and nonalcoholic fatty liver disease
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US10953027B2

  公开（公告）日：2021-03-23

  Disclosed herein are active agents, compositions containing them, unit dosage forms containing them, and methods of their use, e.g., for treating a metabolic disorder or nonalcoholic fatty liver disease or for modulating a metabolic marker or nonalcoholic fatty liver disease marker.

  本文公开了活性剂、含有活性剂的组合物、含有活性剂的单位剂型以及活性剂的使用方法，例如用于治疗代谢紊乱或非酒精性脂肪肝或调节代谢标志物或非酒精性脂肪肝标志物。
• Acylated active agents and methods of their use for the treatment of autoimmune disorders
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US11058698B2

  公开（公告）日：2021-07-13

  Disclosed herein are acylated active agents and methods of their use, e.g., for modulating an autoimmunity marker or for treating an autoimmune disorder.

  本文公开了酰化活性剂及其使用方法，例如用于调节自身免疫标记物或治疗自身免疫性疾病的方法。
• 一种JAK激酶抑制剂的前药
  申请人：[en]E-NITIATE BIOPHARMACEUTICALS (HANGZHOU) CO., LTD;[zh]启元生物（杭州）有限公司

  公开号：WO2024041586A1

  公开（公告）日：2024-02-29

  本发明涉及含JAK抑制剂的前药、组合物及其应用。特别地，本发明涉及式 (II) 所示的化合物、含有本发明化合物的药物组合物，及其作为JAK抑制剂前药在治疗炎症性疾病和肿瘤相关疾病中的用途。