4-[(butoxycarbonyl)amino]benzoic acid | 108245-93-8

• 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: 4-[(butoxycarbonyl)amino]benzoic acid
• 英文别名: 4-Butoxycarbonylamino-benzoesaeure；4-Butoxycarbonylaminobenzoic acid；4-(butoxycarbonylamino)benzoic acid
• CAS: 108245-93-8
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: FNMPBOOKUXXYCR-UHFFFAOYSA-N

物化性质

• 沸点：
  348.7±25.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(butoxycarbonyl)amino]benzoic acid 在 盐酸 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 (3-{4-[(butoxycarbonyl)amino]benzoyloxy}-2-hydroxypropyl)dimethylammonium chloride
  参考文献：
  名称：

  3-（二烷基氨基）-2-羟丙基4-[（（烷氧基-羰基）氨基]苯甲酸酯和它们的季铵盐的合成，分析，抑制胆碱酯酶的活性和分子模型研究。

  摘要：

  合成了叔胺3-（二烷基氨基）-2-羟丙基4-[（烷氧羰基）氨基]苯甲酸酯及其季铵盐。季铵盐的合成的最后一步是通过微波辅助合成进行的。软件计算的数据提供了根据其理化性质比较十五种新化合物的背景。测定了叔胺的酸解离常数（pKa）和亲脂性指数（log P）。季铵盐通过软件计算的亲脂性指数和表面张力表征。生物学评估旨在测试合成化合物的乙酰胆碱酯酶和丁酰胆碱酯酶抑制活性。这些化合物可能的作用机理是通过结合对接技术的分子模型研究确定的。分子动力学模拟和量子力学计算。

  DOI：

  10.3390/molecules22122048
• 作为产物：
  描述：

  对氨基苯甲酸 、 氯甲酸丁酯 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以70%的产率得到4-[(butoxycarbonyl)amino]benzoic acid
  参考文献：
  名称：

  3-（二烷基氨基）-2-羟丙基4-[（（烷氧基-羰基）氨基]苯甲酸酯和它们的季铵盐的合成，分析，抑制胆碱酯酶的活性和分子模型研究。

  摘要：

  合成了叔胺3-（二烷基氨基）-2-羟丙基4-[（烷氧羰基）氨基]苯甲酸酯及其季铵盐。季铵盐的合成的最后一步是通过微波辅助合成进行的。软件计算的数据提供了根据其理化性质比较十五种新化合物的背景。测定了叔胺的酸解离常数（pKa）和亲脂性指数（log P）。季铵盐通过软件计算的亲脂性指数和表面张力表征。生物学评估旨在测试合成化合物的乙酰胆碱酯酶和丁酰胆碱酯酶抑制活性。这些化合物可能的作用机理是通过结合对接技术的分子模型研究确定的。分子动力学模拟和量子力学计算。

  DOI：

  10.3390/molecules22122048

文献信息

• Epoxysuccinamide derivative or salt thereof
  申请人：Taiho Pharmaceuticals Co., Ltd.

  公开号：US06110967A1

  公开（公告）日：2000-08-29

  The invention relates an epoxysuccinamide derivative represented by a formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl or aminoalkyl group, R.sup.2 represents an aminoalkyl group which May be substituted, an aryl group which may be substituted, a heterocyclic group which may be substituted, an aralkyl group which may be substituted, or an alkyl group substituted by a heterocyclic ring which may be substituted, or R.sup.1 and R.sup.2 may form a nitrogen-containing heterocyclic ring, which may be substituted, together with the adjacent nitrogen atoms, and R.sup.3 and R.sup.4 are the same or different from each other and independently represent a hydrogen atom, or an alkyl or aralkyl group, or a salt thereof, a preparation process thereof, and a medicine comprising such a derivative or salt as an active ingredient. This compound has a specific inhibitory activity for cathepsin L and family enzymes thereof, and is useful as an agent for preventing and treating metabolic osteopathy such as osteoporosis and hypercalcemia.

  该发明涉及一种由以下式（I）表示的环氧琥珀酰胺衍生物：##STR1##其中R.sup.1代表氢原子、烷基或氨基烷基基团，R.sup.2代表可能被取代的氨基烷基基团、可能被取代的芳基、可能被取代的杂环基、可能被取代的芳基烷基基团，或者可能被取代的杂环环取代的烷基基团，或者R.sup.1和R.sup.2可以形成含氮杂环环，该环可能被取代，与相邻的氮原子一起，R.sup.3和R.sup.4彼此相同或不同且独立地表示氢原子，或者烷基或芳基烷基基团，或其盐，其制备方法以及包含该衍生物或盐作为活性成分的药物。该化合物具有对半胱氨酸蛋白酶L及其家族酶的特异性抑制活性，并且可用作预防和治疗代谢性骨病如骨质疏松症和高钙血症的药物。
• NOVEL EPOXYSUCCINAMIDE DERIVATIVES OR SALTS THEREOF
  申请人：TAIHO PHARMACEUTICAL COMPANY, LIMITED

  公开号：EP0921122A1

  公开（公告）日：1999-06-09

  The invention relates an epoxysuccinamide derivative represented by a formula (I): wherein R1 represents a hydrogen atom, an alkyl or aminoalkyl group, R2 represents an aminoalkyl group which may be substituted, an aryl group which may be substituted, a heterocyclic group which may be substituted, an aralkyl group which may be substituted, or an alkyl group substituted by a heterocyclic ring which may be substituted, or R1 and R2 may form a nitrogen-containing heterocyclic ring, which may be substituted, together with the adjacent nitrogen atoms, and R3 and R4 are the same or different from each other and independently represent a hydrogen atom, or an alkyl or aralkyl group, or a salt thereof, a preparation process thereof, and a medicine comprising such a derivative or salt as an active ingredient. This compound has a specific inhibitory activity for cathepsin L and family enzymes thereof, and is useful as an agent for preventing and treating metabolic osteopathy such as osteoporosis and hypercalcemia.

  本发明涉及一种环氧琥珀酰胺衍生物，由式（I）表示 由式(I)表示：其中 R1 代表氢原子、烷基或氨基烷基，R2 代表可被取代的氨基烷基、可被取代的芳基、可被取代的杂环基、可被取代的芳烷基或被可被取代的杂环取代的烷基、或 R1 和 R2 可与相邻的氮原子一起形成可被取代的含氮杂环，且 R3 和 R4 彼此相同或不同，并独立代表氢原子或烷基或芳烷基，或其盐，其制备方法，以及包含这种衍生物或盐作为有效成分的药物。该化合物对 cathepsin L 及其家族酶具有特异性抑制活性，可作为预防和治疗骨质疏松症和高钙血症等代谢性骨病的药物。
• Mokry; Zemanova; Csoellei, Pharmazie, 2003, vol. 58, # 1, p. 18 - 21
  作者：Mokry、Zemanova、Csoellei、Racanska、Tumova

  DOI：——

  日期：——
• Searching new structural scaffolds for BRAF inhibitors. An integrative study using theoretical and experimental techniques
  作者：Ludmila E. Campos、Francisco M. Garibotto、Emilio Angelina、Jiri Kos、Tihomir Tomašič、Nace Zidar、Danijel Kikelj、Tomas Gonec、Pavlina Marvanova、Petr Mokry、Josef Jampilek、Sergio E. Alvarez、Ricardo D. Enriz

  DOI：10.1016/j.bioorg.2019.103125

  日期：2019.10

  The identification of the V600E activating mutation in the protein kinase BRAF in around 50% of melanoma patients has driven the development of highly potent small inhibitors (BRAFi) of the mutated protein. To date, Dabrafenib and Vemurafenib, two specific BRAFi, have been clinically approved for the treatment of metastatic melanoma. Unfortunately, after the initial response, tumors become resistant and patients develop a progressive and lethal disease, making imperative the development of new therapeutic options. The main objective of this work was to find new BRAF inhibitors with different structural scaffolds than those of the known inhibitors. Our study was carried out in different stages; in the first step we performed a virtual screening that allowed us to identify potential new inhibitors. In the second step, we synthesized and tested the inhibitory activity of the novel compounds founded. Finally, we conducted a molecular modelling study that allowed us to understand interactions at the molecular level that stabilize the formation of the different molecular complexes.Our theoretical and experimental study allowed the identification of four new structural scaffolds, which could be used as starting structures for the design and development of new inhibitors of BRAF. Our experimental data indicate that the most active compounds reduced significantly ERK1/2 phosphorylation, a measure of BRAF inhibition, and cell viability. Thus, from our theoretical and experimental results, we propose new substituted hydroxynaphthalenecarboxamides, N-(hetero)aryl-piperazinylhydroxyalkylphenylcarbamates, substituted piperazinylethanols and substituted piperazinylpropandiols as initial structures for the development of new inhibitors for BRAF. Moreover, by performing QTAIM analysis, we are able to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analysis indicates which portion of the different molecules must be changed in order to obtain an increase in the binding affinity of these new ligands.
• Najer et al., Bulletin de la Societe Chimique de France, 1955, p. 1189,1190
  作者：Najer et al.

  DOI：——

  日期：——