4-ethyl-N-phenylpiperazine-1-carboxamide

• 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-ethyl-N-phenylpiperazine-1-carboxamide
• 化学式: C₁₃H₁₉N₃O
• 分子量: 233.313
• InChiKey: KAXTVNFTSVCRDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-ethyl-N-phenylpiperazine-1-carboxamide 在 sodium hydride 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 N-((5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-4-ethyl-N-phenylpiperazine-1-carboxamide
  参考文献：
  名称：

  WO2017/23133

  摘要：

  公开号：
• 作为产物：
  描述：

  N-乙基哌嗪 、 异氰酸苯酯 以 乙醚 为溶剂， 反应 18.0h， 以69.5%的产率得到4-ethyl-N-phenylpiperazine-1-carboxamide
  参考文献：
  名称：

  WO2017/23133

  摘要：

  公开号：

文献信息

• Quinoline Derivatives as NK-3 and NK-2 Antagonists
  申请人：Farina Carlo

  公开号：US20070015766A1

  公开（公告）日：2007-01-18

  Certain compounds of formula (I) below or a pharmaceutically acceptable salt or hydrate thereof: wherein: R 1 is H or alkyl; R 2 is aryl, cycloalkyl or heteroaryl; R 3 is H or C 1-3 alkyl, optionally substituted by one or more fluorines; R 4 is H, R 8 NR 9 R 10 , R 11 R 13 or R 11 R 12 R 13 ; or R 5 is branched or linear alkyl, cycloalkyl, aryl, arylalkyl, or a single or fused ring aromatic heterocyclic group; a process for preparing such compounds, a pharmaceutical composition comprising such compounds and the use of such compounds and the use of such compounds and composition in medicine.

  以下式(I)所示的某些化合物或其药学上可接受的盐或水合物： 其中： R1为H或烷基； R2为芳基、环烷基或杂环芳基； R3为H或C1-3烷基，可选择地被一个或多个氟取代； R4为H、R8NR9R10、R11R13或R11R12R13； 或 R5为支链或直链烷基、环烷基、芳基、芳基烷基或单个或融合的环芳杂环基； 一种制备这种化合物的方法，包括这种化合物的制药组合物，以及这种化合物和组合物在医药中的使用。
• 1,3,4-oxadiazole derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same
  申请人：Chong Kun Dang Pharmaceutical Corp.

  公开号：US10717716B2

  公开（公告）日：2020-07-21

  The present invention relates to novel compounds having histone deacetylase 6 (HDAC6) in-hibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions containing the same, a method for treating diseases using the composition, and methods for preparing the novel compounds. The novel compounds stereoisomers thereof or pharmaceutically acceptable salts thereof according to the present invention have histone deacetylase (HDAC) inhibitory activity and are effective for the prevention or treatment of HDAC6-mediated diseases, including infectious diseases; neoplasms; endocrine, nutritional and metabolic diseases; mental and be-havioral disorders; neurological diseases; diseases of the eye and adnexa; cardiovascular diseases; respiratory diseases; digestive diseases; diseases of the skin and subcutaneous tissue; diseases of the musculoskeletal system and connective tissue; or congenital malformations, deformations and chromosomal abnormalities.

  本发明涉及具有组蛋白去乙酰化酶6(HDAC6)抑制活性的新型化合物、其立体异构体或其药学上可接受的盐，其在制备治疗药物中的用途，含有其的药物组合物，使用该组合物治疗疾病的方法，以及制备该新型化合物的方法。根据本发明的新型化合物立体异构体或其药学上可接受的盐具有组蛋白去乙酰化酶（HDAC）抑制活性，可有效预防或治疗HDAC6介导的疾病，包括感染性疾病、肿瘤、内分泌、营养和代谢性疾病；精神和行为障碍；神经系统疾病；眼睛和附件疾病；心血管疾病；呼吸系统疾病；消化系统疾病；皮肤和皮下组织疾病；肌肉骨骼系统和结缔组织疾病；或先天性畸形、变形和染色体异常。
• 1,3,4-OXADIAZOLE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  申请人：Chong Kun Dang Pharmaceutical Corp.

  公开号：EP3331864B1

  公开（公告）日：2021-11-03
• WO2017/23133
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery and optimization of aspartate aminotransferase 1 inhibitors to target redox balance in pancreatic ductal adenocarcinoma
  作者：Justin Anglin、Reza Beheshti Zavareh、Philipp N. Sander、Daniel Haldar、Edouard Mullarky、Lewis C. Cantley、Alec C. Kimmelman、Costas A. Lyssiotis、Luke L. Lairson

  DOI：10.1016/j.bmcl.2018.04.061

  日期：2018.9

  Pancreatic ductal adenocarcinoma (PDAC) is a lethal malignancy that is extremely refractory to the therapeutic approaches that have been evaluated to date. Recently, it has been demonstrated that PDAC tumors are dependent upon a metabolic pathway involving aspartate aminotransferase 1, also known as glutamate-oxaloacetate transaminase 1 (GOT1), for the maintenance of redox homeostasis and sustained proliferation. As such, small molecule inhibitors targeting this metabolic pathway may provide a novel therapeutic approach for the treatment of this devastating disease. To this end, from a high throughput screen of similar to 800,000 molecules, 4-(1H-indol-4-yl)-N-phenylpiperazine-1-carboxamide was identified as an inhibitor of GOT1. Mouse pharmacokinetic studies revealed that potency, rather than inherent metabolic instability, would limit immediate cell- and rodent xenograft-based experiments aimed at validating this potential cancer metabolism-related target. Medicinal chemistry-based optimization resulted in the identification of multiple derivatives with >10-fold improvements in potency, as well as the identification of a tryptamine-based series of GOT1 inhibitors. (C) 2018 Elsevier Ltd. All rights reserved.