methyl 2-(3-aminophenyl)-2-((tert-butoxycarbonyl)amino)acetate | 180081-34-9

• 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
• 英文名称: methyl 2-(3-aminophenyl)-2-((tert-butoxycarbonyl)amino)acetate
• 英文别名: methyl (3-aminophenyl)[(tert-butoxycarbonyl)amino]acetate；2-(3-aminophenyl)-2-t-butoxycarbonylaminoacetic acid methyl ester；(3-aminophenyl)tert-butoxycarbonylaminoacetic acid methyl ester；methyl 2-(3-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 180081-34-9
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: JSWIXCXPTGPDBA-UHFFFAOYSA-N

物化性质

• 沸点：
  445.0±40.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-aminophenyl)-2-((tert-butoxycarbonyl)amino)acetate 在 吡啶 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 3-({3-[carboxy(carboxyamino)methyl]phenyl}sulfamoyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of non-covalent AmpC β-lactamases inhibitors

  摘要：

  Bacterial resistance represents a worldwide emergency threatening the efficacy of all available antibiotics. Among the several resistance mechanisms developed by bacteria, beta-lactamase enzymes (BLs), which are able to inactivate most beta-lactam core antibiotics, represent a key target to block, thus prolonging antibiotics half-life. Several approaches aimed at inhibiting beta-lactamases have been so far undertaken, mainly involving beta-lactam-like or covalent inhibitors. Applying a structure-based de novo design approach, we recently discovered a novel, non-covalent and competitive inhibitor of AmpC beta-lactamase: lead 1. It has a K-i of 1 mu M, a ligand efficiency of 0.38 kcal mol(-1) and lead-like physical properties. Moreover, it reverts resistance to ceftazidime in bacterial pathogens expressing AmpC and does not up-regulate beta-lactamases expression in cell culture. Its features make it a good candidate for chemical optimization: starting from lead 1 crystallographic complex with AmpC, 11 analogs were designed to complement additional AmpC sites, then synthesized and tested against clinically resistant pathogens. While the new inhibitors maintain similar in vitro activity as the starting lead, some of them, in biological assays, extert a higher potency showing improved synergic activity with ceftazidime in resistant clinically isolated strains.

  DOI：

  10.1007/s00044-017-1809-x
• 作为产物：
  描述：

  3-硝基苯乙酸 以27%的产率得到methyl 2-(3-aminophenyl)-2-((tert-butoxycarbonyl)amino)acetate
  参考文献：
  名称：

  Aniline derivatives possessing an inhibitory effect of nitric oxide synthase

  摘要：

  由一般式（1）表示的化合物：（其中R1为SR6或NR7R8，其中R6通常为具有1-6个碳原子的烷基基团，R7为氢原子、具有1-6个碳原子的烷基基团或硝基基团，R8为氢原子或具有1-6个碳原子的烷基基团；R2和R3通常为氢原子或具有1-6个碳原子的烷基基团；R4为氢原子、具有1-6个碳原子的烷基基团或其胺部分可能被烷基或硝基基团取代的酰胺基团；R5为氢原子或具有1-6个碳原子的烷基基团；Y1、Y2、Y3和Y4可能相同或不同，通常为氢原子、卤素原子或具有1-6个碳原子的烷氧基团；n和m各自为0或1的整数），或这些化合物的可能立体异构体或光学活性形式，或其药学上可接受的盐。这些化合物具有强效的一氧化氮合酶抑制活性，并可用作脑血管疾病的治疗药物。

  公开号：

  US06534546B1

文献信息

• [EN] GASTRIN AND CHOLECYSTOKININ RECEPTOR LIGANDS<br/>[FR] LIGANDS DES RECEPTEURS DE LA GASTRINE ET DE LA CHOLECYSTOKININE
  申请人：BLACK JAMES FOUNDATION

  公开号：WO2000027823A1

  公开（公告）日：2000-05-18

  Compounds of formula (I) and their pharmaceutically acceptable salts are ligands at gastrin and/or cholecystokinin receptors. X and Y are independently =N-, -N(R5)- =CH-, -S- or -O-. n is from 1 to 4; R1 is H or C¿1? to C15 hydrocarbyl R?2¿ is selected from H, Me, Et, Pr and OH, R¿3? is selected from H, Me, Et and Pr; or (when n is greater than 1) each R?3¿ is independently selected from H, Me, Et and Pr, or two R3 groups on neighbouring carbon atoms are linked to form a C¿3? to C6 carbocylic ring, or R?2 and R3¿ on the same carbon atom together represent an =O group; R4 is C1 to C15 hydrocarbyl Z is -(NR7)a-CO-(NR8)b- (wherein a is 0 or 1, b is 0 or 1, -CO-NR7-CH2-CO-NR8-, -CO-O-, -CH¿2?-CH2-, -CH=CH-, -CH2-NR?8¿- or a bond; Q is -R9V, or (II), (wherein R9 is -CH¿2?-; -CH2-CH2-; or (III), R?9 and R8¿, together with the nitrogen atom to which R8 is attached, form a piperidine or pyrrolidine ring which is substituted by V; V is -CO-NH-SO¿2?-Ph, -SO2-NH-CO-Ph, -CH2OH, or a group of the formula -R?10¿U, (wherein U is -COOH, tetrazolyl, -CONHOH- or -SO¿3?H; and R?10¿ is a bond; C¿1? to C6 hydrocarbylene, -O-(C1 to C3 alkylene)-; -SO2NR?11-CHR12¿-; -CO-NR?11-CHR12¿-, or -NH-(CO)¿c?-CH2-, c being 0 or 1).

  式(I)化合物及其药学上可接受的盐是胃泌素和/或胆囊收缩素受体的配体。X和Y独立地为=N-，-N（R5）-，=CH-，-S-或-O-。n为1至4；R1为H或C1至C15的烃基；R2从H，Me，Et，Pr和OH中选择，R3从H，Me，Et和Pr中选择；或（当n大于1时）每个R3独立地从H，Me，Et和Pr中选择，或相邻碳原子上的两个R3基团连接形成C3至C6的环烷基，或R2和R3在同一碳原子上共同表示一个=O基团；R4为C1至C15的烃基，Z为-(NR7)a-CO-(NR8)b-（其中a为0或1，b为0或1，-CO-NR7-CH2-CO-NR8-，-CO-O-，-CH2-CH2-，-CH=CH-，-CH2-NR8-或键；Q为-R9V，或（II），（其中R9为-CH2-；-CH2-CH2-；或（III），R9和R8，连同R8所连接的氮原子，形成被V取代的哌嗪或吡咯烷环；V为-CO-NH-SO2-Ph，-SO2-NH-CO-Ph，-CH2OH，或式-R10U的基团（其中U为-COOH，四唑基，-CONHOH-或-SO3H；R10为键；C1至C6的烃亚基，-O-（C1至C3的烷基）-；-SO2NR11-CHR12-；-CO-NR11-CHR12-，或-NH-（CO）c-CH2-，其中c为0或1）。
• 2-Aminooxazolines as TAAR1 ligands
  申请人：Galley Guido

  公开号：US20080261920A1

  公开（公告）日：2008-10-23

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及化合物I的公式，其中X，Y，R1，R2和n如本文所定义，或其药学上适宜的酸加盐。本发明还涉及含有这种化合物的制药组合物和治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍、压力相关障碍、精神障碍、精神分裂症、神经系统疾病、帕金森病、神经退行性疾病、阿尔茨海默病、癫痫、偏头痛、物质滥用和代谢性疾病、进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。
• 2-AMINOOXAZOLINES AS TAAR1 LIGANDS
  申请人：Galley Guido

  公开号：US20100120864A1

  公开（公告）日：2010-05-13

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中X，Y，R1，R2和n如本文所定义，或其药学适宜的酸加盐。本发明还涉及含有此类化合物的制药组合物，以及用于治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症，焦虑症，双相情感障碍，注意力缺陷多动障碍，应激相关障碍，精神疾病，精神分裂症，神经疾病，帕金森病，神经退行性疾病，阿尔茨海默病，癫痫，偏头痛，物质滥用和代谢性疾病，进食障碍，糖尿病，糖尿病并发症，肥胖症，血脂异常，能量消耗和吸收障碍，体温稳态障碍和功能障碍，睡眠和生物钟节律障碍以及心血管疾病。
• 2-aminooxazolines as TAAR1 ligands
  申请人：Galley Guido

  公开号：US08604061B2

  公开（公告）日：2013-12-10

  The invention relates to compounds of formula I wherein X, Y, R1, R2, and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中X、Y、R1、R2和n如本文所定义，或其药学上适宜的酸加盐。本发明还涉及含有这种化合物的制药组合物和治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症、焦虑症、躁郁症、注意力缺陷多动障碍、与压力相关的疾病、精神疾病、精神分裂症、神经系统疾病、帕金森病、神经退行性疾病、阿尔茨海默病、癫痫、偏头痛、物质滥用和代谢性疾病、进食障碍、糖尿病、糖尿病并发症、肥胖症、脂质代谢异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。
• WO2008/92785
  申请人：——

  公开号：——

  公开（公告）日：——