1-adamantyl p-nitrobenzoate | 968-84-3

• 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: 1-adamantyl p-nitrobenzoate
• 英文别名: 1-adamantyl 4-nitrobenzoate；1-Adamantyl-p-nitrobenzoat；Adamantan-1-yl p-nitrobenzoate
• CAS: 968-84-3
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: RSHLYJFLTWZSHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-adamantyl p-nitrobenzoate 在 potassium acetate 作用下， 以 水 、 乙腈 为溶剂， 生成 1-金刚烷醇
  参考文献：
  名称：

  1-和3-高金刚烷基-对硝基苯甲酸酯在乙腈-水中的溶剂分解（重量比为70:30）

  摘要：

  报告了叔丁基，1-金刚烷基，3-和1-高金刚烷基-对硝基苯甲酸酯在乙腈-水中的溶剂分解速率（按重量计70:30），并讨论了相对速率。这些是具有明确已知结构的1-或3-高金刚烷基酯的第一溶剂分解常数。

  DOI：

  10.1016/s0040-4039(00)86747-7
• 作为产物：
  描述：

  金刚烷 、 对硝基苯甲酸 在 戊腈 、 Selectfluor 、 copper(ll) bromide 作用下， 以 硝基甲烷 为溶剂， 反应 4.0h， 以72%的产率得到1-adamantyl p-nitrobenzoate
  参考文献：
  名称：

  未活化的C（sp 3）–H键通过交叉脱氢偶联反应与羧酸的铜催化氧化酯化†

  摘要：

  已经开发出一种以Selectfluor为氧化剂对烃的未活化（非苄基和烯丙基）C（sp 3）-H键进行有效的铜催化酯化反应。该反应可以为通过酯水解合成酯和烷基醇提供直接，新的和有用的策略。

  DOI：

  10.1039/c4ra14586k

文献信息

• Synthesis, structure–activity relationship, and p210bcr-abl protein tyrosine kinase activity of novel AG 957 analogs☆
  作者：Gurmeet Kaur、Ven L. Narayanan、Prabhakar A. Risbood、Melinda G. Hollingshead、Sherman F. Stinson、Ravi K. Varma、Edward A. Sausville

  DOI：10.1016/j.bmc.2004.12.003

  日期：2005.3.1

  A series of novel, sterically hindered lipophilic analogs of AG 957 was designed and synthesized as potential protein tyrosine kinase (PTK) inhibitors. The in vitro activity, in vivo anti-leukemia activity, and pharmacology of these PTK inhibitors were studied. Some aspects of the structure-activity relationship associated with the carboxylic acid, phenol ring, and linker modifications are discussed

  设计并合成了一系列新型的，空间受限的AG 957亲脂性类似物，作为潜在的蛋白酪氨酸激酶（PTK）抑制剂。研究了这些PTK抑制剂的体外活性，体内抗白血病活性和药理作用。讨论了与羧酸，苯酚环和连接基修饰相关的结构活性关系的某些方面。我们已经证明1，4-氢醌部分对于活性是必不可少的，并且位阻酯有助于增强体内功效。Adaphostin（NSC 680410）已作为改良的化合物出现，具有最大的体内抗白血病中空纤维活性，与最初的铅化合物AG 957一致。目前，adaphostin正在临床前毒理学研究中。
• Disubstituted lavendustin A analogs and pharmaceutical compositions comprising the analogs
  申请人：THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1367046A9

  公开（公告）日：2004-05-12

  Disubstituted lavendustin A analogs that are PTK inhibitors having antiproliferative activity are described. Preferred compounds of the present invention, without limitation, satisfy either Formula 1 or Formula 2. Currently preferred compounds ,based on in vivo biological activity, are 4'-adamantylbenzoate-1'-N-1,4-dihydroxybenzylamine and 4'-adamantylmethylbenzoate-1'-N-1,4-dihydroxybenzylamine. The present invention also provides pharmaceutical compositions comprising effective amounts of disubstituted lavendustin A analogs. Such compositions also may comprise other active ingredients, other materials conventionally used in the formulation of pharmaceutical composition, and mixtures thereof. The compounds and compositions of the present invention can be used for treating subjects to, for example, inhibit the proliferation of living cells in the treatment of proliferative diseases.

  描述了具有抗增殖活性的PTK抑制剂的二取代拉文杜斯汀A类似物。本发明的优选化合物，不受限于，满足Formula 1或Formula 2中的任一种。根据体内生物活性，目前优选的化合物是4'-金刚烷基苯甲酸酯-1'-N-1,4-二羟基苯乙胺和4'-金刚烷基甲基苯甲酸酯-1'-N-1,4-二羟基苯乙胺。本发明还提供了含有二取代拉文杜斯汀A类似物有效量的药物组合物。这种组合物还可以包括其他活性成分、传统用于制备药物组合物的其他材料以及它们的混合物。本发明的化合物和组合物可用于治疗受试者，例如，在治疗增殖性疾病中抑制活细胞的增殖。
• Disubstituted lavendustin A analogs and pharmaceutical composition comprising the analogs
  申请人：Narayanan Venkatachala L.

  公开号：US06943191B1

  公开（公告）日：2005-09-13

  Disubstituted lavendustin A analogs that are PTK inhibitors having antiproliferative activity are described. Preferred compounds of the disclosure, without limitation, satisfy either Formula 1 or Formula 2. The present disclosure also provides pharmaceutical compositions comprising effective amounts of disubstituted lavendustin A analogs and potentially comprising other active ingredients, other materials conventionally used in the formulation of pharmaceutical compositions, and mixtures thereof. The compounds and compositions of the disclosure can be used for treating subjects to, for example, inhibit the proliferation of living cells in the treatment of proliferative diseases.

  本文介绍了具有抗增殖活性的PTK抑制剂的二取代lavendustin A类似物。本文披露的优选化合物不受限于满足公式1或公式2的化合物。本文还提供了含有有效量的二取代lavendustin A类似物的制药组合物，可能还包括其他活性成分、传统用于制药组合物配方的其他材料以及它们的混合物。本文所述的化合物和组合物可用于治疗主题，例如在增殖性疾病治疗中抑制活细胞的增殖。
• Disubstituted lavendustin a analogs and pharmaceutical compositions comprising the analogs
  申请人：THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1367046A1

  公开（公告）日：2003-12-03

  Disubstituted lavendustin A analogs that are PTK inhibitors having antiproliferative activity are described. Preferred compounds of the present invention, without limitation, satisfy either Formula 1 or Formula 2. Currently preferred compounds ,based on in vivo biological activity, are 4'-adamantylbenzoate-1'-N-1,4-dihydroxybenzylamine and 4'-adamantylmethylbenzoate-1'-N-1,4-dihydroxybenzylamine. The present invention also provides pharmaceutical compositions comprising effective amounts of disubstituted lavendustin A analogs. Such compositions also may comprise other active ingredients, other materials conventionally used in the formulation of pharmaceutical composition, and mixtures thereof. The compounds and compositions of the present invention can be used for treating subjects to, for example, inhibit the proliferation of living cells in the treatment of proliferative diseases.

  本发明描述了具有抗增殖活性的 PTK 抑制剂--二取代的拉芬多汀 A 类似物。本发明的优选化合物不限于满足式 1 或式 2。根据体内生物活性，目前优选的化合物是 4'-金刚烷基苯甲酸-1'-N-1,4-二羟基苄胺和 4'-金刚烷基甲基苯甲酸-1'-N-1,4-二羟基苄胺。本发明还提供了包含有效量的二取代拉芬多汀 A 类似物的药物组合物。此类组合物还可包含其他活性成分、用于配制药物组合物的其他常规材料及其混合物。本发明的化合物和组合物可用于治疗受试者，例如在治疗增殖性疾病时抑制活细胞的增殖。
• Synthesis and biological evaluation of platensic alcohol as an adamantane surrogate in antitumor drug lead adaphostin
  作者：Zhongqing Wen、Yanwen Duan、Yi Xiong、Yong Huang

  DOI：10.1016/j.bmcl.2021.128270

  日期：2021.9