N-(tert-butoxycarbonyl)-N'-(3-chlorophenyl)-ethylenediamine | 183500-67-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(tert-butoxycarbonyl)-N'-(3-chlorophenyl)-ethylenediamine
• 英文别名: tert-butyl N-[2-(3-chloroanilino)ethyl]carbamate
• CAS: 183500-67-6
• 化学式: C₁₃H₁₉ClN₂O₂
• 分子量: 270.759
• InChiKey: ZUSPXVZVYRCDTB-UHFFFAOYSA-N

物化性质

• 沸点：
  425.3±25.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-N'-(3-chlorophenyl)-ethylenediamine 在 盐酸 、 4 A molecular sieve 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 生成 4-[1-(4-Cyanobenzyl)-5-imidazolylmethyl]-1-(3-chlorophenyl)-piperazine-2,3-dione
  参考文献：
  名称：

  Oxo-piperazine Derivatives of N-Arylpiperazinones as Inhibitors of Farnesyltransferase

  摘要：

  The evaluation of SAR associated with the insertion of carbonyl groups at various positions of N-arylpiperazinone farnesyltransferase inhibitors is described herein. 1-Aryl-2,3-diketopiperazine derivatives exhibited the best balance of potency and pharmacokinetic profile relative to the parent 1-aryl-2-piperazinones. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00710-1
• 作为产物：
  描述：

  [(3-chlorophenylcarbamoyl)methyl]carbamic acid t-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-(tert-butoxycarbonyl)-N'-(3-chlorophenyl)-ethylenediamine
  参考文献：
  名称：

  Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases

  摘要：

  In our previous work, 3I inhibited the LPS-induced iNOS activity and NO production in RAW 264.7 cells and improved joint inflammation and cartilage destruction in inflammatory model. In this study, we synthesized 59 derivatives and bioisosteres on the basis of 3I by Knoevenagel condensation and biologically evaluated for the study of structure-activity relationship (SAR). We found that 7-44 suppressed the iNOS activity (IC50 25.2 mu M) and LPS-induced NO production (IC50 45.6 mu M) in RAW 264.7 cells. As for the SAR study, the dimethoxylphenyl group of 7-44 was potential for a further modification. At a dose of 10 mg/kg, oral administration of 7-44 possessed protective properties in both carrageenan-induced paw edema of male ICR mice and adjuvant-induced arthritis of Lewis female rats. Although the activity of 7-44 was slightly inferior, the PK profiles of 7-44 were superior to those of 3I. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.036

文献信息

• Inhibitors of farnesyl-protein transferase
  申请人：Merck & Co., Inc.

  公开号：US06001835A1

  公开（公告）日：1999-12-14

  The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.

  本发明涉及抑制法尼基-蛋白转移酶（FTase）和致癌基因蛋白Ras的法尼醇化的化合物。该发明进一步涉及含有本发明化合物的化疗组合物以及用于抑制法尼基-蛋白转移酶和致癌基因蛋白Ras的法尼醇化的方法。
• Method of treating cancer
  申请人：——

  公开号：US20030220241A1

  公开（公告）日：2003-11-27

  The present invention relates to methods of treating cancer using a combination of a compound which is a PSA conjugate and a compound which is a inhibitor of prenyl-protein transferase, which methods comprise administering to said mammal, either sequentially in any order or simultaneously, amounts of at least two therapeutic agents selected from a group consisting of a compound which is a PSA conjugate and a compound which is a inhibitor of prenyl-protein transferase. The invention also relates to methods of preparing such compositions.

  本发明涉及使用一种PSA共轭物和一种前脂蛋白转移酶抑制剂的组合治疗癌症的方法，该方法包括向所述哺乳动物施用来自以下组中选择的至少两种治疗剂的量，所述组包括一种PSA共轭物和一种前脂蛋白转移酶抑制剂，所述治疗剂可以顺序给药或同时给药。该发明还涉及制备这种组合物的方法。
• Inhibitors of prenyl-protein transferase
  申请人：——

  公开号：US20020010184A1

  公开（公告）日：2002-01-24

  The present invention comprises piperazinone-containing compounds which inhibit prenyl-protein transferases, including famesyl-protein transferase and geranylgeranyl-protein transferase type I. Such therapeutic compounds are useful in the treatment of cancer.

  该发明涉及含有哌嗪酮类化合物，可抑制前列蛋白转移酶，包括法美基蛋白转移酶和戈楞基蛋白转移酶I型。这种治疗性化合物对癌症的治疗具有用处。
• [EN] INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE FARNESYL-PROTEINE TRANSFERASE
  申请人：MERCK & CO., INC.

  公开号：WO1996030343A1

  公开（公告）日：1996-10-03

  (EN) The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.(FR) La présente invention concerne des composés qui inhibent la farnésyl-protéine transférase (FTase) et la farnélysation de l'oncogène Ras protéique. L'invention concerne en outre des compositions chimiothérapeutiques contenant les composés de cette invention, et des procédés servant à inhiber la farnésyl-protéine transférase et la farnélysation de la protéine d'oncogène Ras.

  该发明涉及抑制法尼酰-蛋白转移酶（FTase）和癌基因蛋白Ras的法尼酰化的化合物。该发明进一步涉及含有该发明化合物的化疗组合物和抑制法尼酰-蛋白转移酶和癌基因蛋白Ras的法尼酰化的方法。
• Discovery of N-(2-aminoethyl)-N-benzyloxyphenyl benzamides: New potent Trypanosoma brucei inhibitors
  作者：Andriy Buchynskyy、J. Robert Gillespie、Matthew A. Hulverson、Joshua McQueen、Sharon A. Creason、Ranae M. Ranade、Nicole A. Duster、Michael H. Gelb、Frederick S. Buckner

  DOI：10.1016/j.bmc.2016.11.019

  日期：2017.3

  A phenotypic screen of a compound library for antiparasitic activity on Trypanosoma brucei, the causative agent of Human African Trypanosomiasis (HAT), led to the identification of N-(2-aminoethyl)-N-phenyl benzamides as a starting point for hit-to-lead medicinal chemistry. Eighty two analogues were prepared, which led to the identification of a set of highly potent N-(2-aminoethyl)-N-benzyloxyphenyl benzamides with the most potent compound 73 having an in vitro EC50 = 0.001 mu M. The compounds displayed drug like properties when tested in a number of in vitro assays. Compound 73 was orally bioavailable and displayed good plasma and brain exposure in mice, cured 2 out of 3 mice infected with Trypanosoma brucei in acute model when dosed orally at 50 mg/kg once per day for 4 days. Given its potent antiparasitic properties and its ease of synthesis, compound 73 represents a potential lead for the development of drug to treat Human African Trypanosomiasis. (C) 2016 Elsevier Ltd. All rights reserved.