tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate | 180138-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate
• 英文别名: 3,6-acridinediylbiscarbamic acid di-tert-butyl ester；tert-butyl N-[6-[(2-methylpropan-2-yl)oxycarbonylamino]acridin-3-yl]carbamate
• CAS: 180138-03-8
• 化学式: C₂₃H₂₇N₃O₄
• 分子量: 409.485
• InChiKey: WEKPBLOGZRDGOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate 、 (2-Chloro-ethyl)-bis-(1-trityl-1H-imidazol-4-ylmethyl)-amine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以54%的产率得到
  参考文献：
  名称：

  Syntheses of imidazole-acridine conjugates as ribonuclease A mimics

  摘要：

  As a result of efforts to mimic the activity of RNase A we report the syntheses of two novel molecules 1 and 2 containing imidazole residues conjugated to an acridine, a well known intercalator and as such these molecules simultaneously have substrate recognition and potential catalytic ability. t-RNA cleavage by I and 2 is reported. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00843-x
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 Cd/Pb amalgam 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 1.0h， 生成 tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate
  参考文献：
  名称：

  Application of 2,2,2-Trichloroethoxycarbonyl Protection to Aminoacridines

  摘要：

  2,2,2-三氯乙氧基羰基 (Troc) 基团已成功用作氨基吖啶的保护基团。与脂肪胺不同，这些芳香胺的脱保护会产生大量 (12-29%) 稳定的 2,2-二氯乙氧基羰基 (Dioc) 副产物。通过引入丁氧羰基（Boc）部分作为临时保护基团形成双氨基甲酸酯，有效解决了这个问题。

  DOI：

  10.1055/s-2006-958951

文献信息

• Bisacridines with aromatic linking chains. Synthesis, DNA interaction, and antitumor activity
  作者：Antonio Lorente、Yolanda Vázquez、Marı́a-José Fernández、Abel Ferrández

  DOI：10.1016/j.bmc.2004.06.021

  日期：2004.8

  Synthesis of a series of bisacridine derivatives containing rigid aromatic linking chains is described. Their DNA interaction and in vitro cytotoxicity against HT-29 human carcinoma cells are reported.

  描述了一系列含有刚性芳族连接链的双ac啶衍生物的合成。据报道它们对HT-29人癌细胞的DNA相互作用和体外细胞毒性。
• Therapeutic acridone and acridine compounds
  申请人：Neidle Stephen

  公开号：US20050070568A1

  公开（公告）日：2005-03-31

  This invention pertains to certain acridine and acridine compounds of the formula (1) which inhibit telomerase, regulate cell proliteration, etc., and/or treat cancer proliferative conditions, etc.: wherein either: (a) K is ═O, L is —H, alpha single bond beta is a double bond, gamma is a single bond (acridines); or, (b) K is a 9-substituent, L is absent, alpha is a double bond, beta is a single bond, gamma is a double bond (acridines); and wherein: J 1 is a 2- or 3-substituent; J 2 is a 6- or 7-substituent; J 1 and J 2 are each a group of the formula —N(R N )—W, wherein: R N is a nitrogen substituent and is hydrogen, C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl, and is optionally substituted; and, W is C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl, and is optionally substitute; and wherein when K is a 9-substituent, K is a group of the formula —N(R N )-Q, wherein: R N is an amino substituent and is hydrogen, C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl; and, Q is C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl, and is optionally substituted; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates, and protected forms thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit telomerase, to regulate cell proliferation, etc., and/or in the treatment of cancer, proliferative conditions, etc.

  本发明涉及某些式(1)的吖啶和吖啶化合物，它们能抑制端粒酶，调节细胞增殖等、和/或治疗癌症增殖性病症等：其中：(a) K 是═O，L 是-H，α 单键 β 是双键，γ 是单键（吖啶类）；或者，(b) K 是 9-取代基，L 不存在，α 是双键，β 是单键，γ 是双键（吖啶类）；以及其中：J 1 是 2-或 3-取代基；J 2 是 6-或 7-取代基；J 1 和 J 2 均为式-N(R) N )-W，其中R N 是氮取代基，并且是氢、C 1-7 烷基、C 3-20 杂环基，或 C 5-20 芳基，并被任选取代；以及 1-7 烷基、C 3-20 杂环基，或 C 5-20 其中，当 K 为 9-取代基时，K 为式 -N(R)-N(R)-N(R)-N(R)-N(R)-N(R)的基团。 N )-Q，其中R N 是氨基取代基，并且是氢、C 1-7 烷基、C 3-20 杂环基，或 C 5-20 芳基；以及 1-7 烷基、C 3-20 杂环基，或 C 5-20 芳基，且任选被取代；及其药学上可接受的盐、酯、酰胺、溶剂、水合物和保护形式。本发明还涉及包含此类化合物的药物组合物，以及此类化合物和组合物在体外和体内抑制端粒酶、调节细胞增殖等和/或治疗癌症、增殖性疾病等方面的用途。
• Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine
  作者：Yohann Benchabane、Carole Di Giorgio、Gérard Boyer、Anne-Sophie Sabatier、Diane Allegro、Vincent Peyrot、Michel De Méo

  DOI：10.1016/j.ejmech.2009.01.010

  日期：2009.6

  The cytotoxicity and photo-enhanced cytotoxicity of a series of 18 3,6-di-substituted acridines were evaluated on both tumour CHO cells and human normal keratinocytes, and compared to their corresponding clastogenicity as assessed by the micronucleus assay.Compounds 2f tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate and 2d N-[6-(pivalamino)acridin-3-yl]pivalamide displayed a specific cytotoxicity on CHO cells. These results suggested that the two derivatives could be considered as interesting candidates for anticancer chemotherapy and hypothesized that the presence of 1,1-dimethylethyl substituents was responsible for a strong non-clastogenic cytotoxicity. Compounds 2b and 2c, on the contrary, displayed a strong clastogenicity. They indicated that the presence of nonbranched aliphatic chains on positions 3 and 6 of the acridine rings tended to induce a significant clastogenic effect. Finally, they established that most of the acridine compounds could be photo-activated by UVA-visible rays and focussed on the significant role of light irradiation on their biological properties. (C) 2009 Elsevier Masson SAS. All rights reserved.
• THERAPEUTIC ACRIDONE AND ACRIDINE COMPOUNDS
  申请人：Cancer Research Technology Limited

  公开号：EP1474397A1

  公开（公告）日：2004-11-10
• US7205311B2
  申请人：——

  公开号：US7205311B2

  公开（公告）日：2007-04-17