4-(5-bromo-2-pyrimidinyloxy)-3-methylaniline | 111986-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(5-bromo-2-pyrimidinyloxy)-3-methylaniline
• 英文别名: 4-(5-bromopyrimidin-2-yloxy)-3-methyl-phenylamine；4-((5-bromopyrimidin-2-yl)oxy)-3-methylaniline；4-(5-bromopyrimidin-2-yl)oxy-3-methylaniline
• CAS: 111986-57-3
• 化学式: C₁₁H₁₀BrN₃O
• 分子量: 280.124
• InChiKey: OEWIWUZEIBYJLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-bromo-2-pyrimidinyloxy)-3-methylaniline 在 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 N-[[4-(5-bromopyrimidin-2-yl)oxy-3-methylphenyl]-phenylsulfanylcarbamoyl]-2-nitrobenzamide
  参考文献：
  名称：

  苯甲酰基苯基脲的前药的合成及其抗肿瘤活性。

  摘要：

  合成了各种苯甲酰基苯基脲衍生物作为候选前药，并在体内检查了它们对P388白血病的抗肿瘤活性。所有的前药都可溶于大多数有机溶剂，并且在腹膜内或口服时对小鼠的P388白血病细胞显示出良好的抗肿瘤活性。

  DOI：

  10.1248/cpb.42.57
• 作为产物：
  描述：

  2-甲基-4-氨基苯酚 、 4-氨基-2-(甲氧基甲基)-苯酚 生成 4-(5-bromo-2-pyrimidinyloxy)-3-methylaniline
  参考文献：
  名称：

  N-benzoyl urea compounds, antitumorous compositions containing them

  摘要：

  一种具有以下化学式的N-苯甲酰脲化合物：其中X是氢原子、卤素原子或硝基基团，n是1到3之间的整数，Q是其中Y1是未取代或取代的烷基基团，或者是烷氧基或烷氧羰基基团，其烷基基团未取代或取代，Y2是氢原子、卤素原子、硝基基团、未取代或取代的烷基基团，或者是烷氧基或烷氧羰基基团，其烷基基团未取代或取代，Z是氢原子、卤素原子、三氟甲基基团或硝基基团，A和B中的每一个是.dbd.CH--或氮原子，前提是A和B中的一个是.dbd.CH--，另一个是氮原子，条件是（1）当Q是时，其中当X是氢原子且Y1是烷基时，Z不是氢原子、卤素原子或三氟甲基基团，以及（2）当Q是时，其中A是氮原子且Y1是三氟甲基基团时，Y2不是氢原子。

  公开号：

  US04863924A1

文献信息

• Substituted benzene derivatives, processes for their production and
  申请人：Ishihara Sangyo Kaisha Ltd.

  公开号：US04987135A1

  公开（公告）日：1991-01-22

  A substituted benzene derivative represented by a formula: ##STR1## where A represents: ##STR2## wherein X is a hydrogen atom, a halogen atom or a nitro group, R.sup.1 is --X.sup.1 Z.sup.1 (X.sup.1 is an oxygen atom or a sulfur atom and Z.sup.1 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group), --COZ.sup.1 group (Z.sup.1 is as defined above), ##STR3## group (Z.sup.1 is as defined above, Z.sup.2 is --CO.sub.2 Z.sup.3 wherein Z.sup.3 is the same as Z.sup.1, or --SO.sub.2 Z.sup.3 wherein Z.sup.3 is as defined above and n is 0 or 1), ##STR4## (Z.sup.1 and Z.sup.3 are as defined above) or ##STR5## (X.sup.2, X.sup.3 and X.sup.4 are, respectively, an oxygen atom or a sulfur atom and Z.sup.4 and Z.sup.5 are the same as Z.sup.1), and R.sup.3 is a nitro group or ##STR6## (R.sup.4 and R.sup.5 are, respectively, an alkyl group, or they may form a heterocyclic group together with the adjacent nitrogen atom), or ##STR7## wherein X and R.sup.3 are as defined above and R.sup.2 is --X.sup.1 Z.sup.1 (X.sup.1 and Z.sup.1 are as defined above); Y is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a nitro group or ##STR8## (R.sup.6 and R.sup.7 are, respectively, a substituted or unsubstituted alkyl group); R is ##STR9## (R.sup.8 is the same as Y and q is an integer of 1 to 4), ##STR10## (R.sup.8 is as defined above, and r is an integer of 1 to 3) or ##STR11## (R.sup.8 and r are defined above); and m is an integer, of 1 to 4, or its salt.

  一个以下式表示的取代苯衍生物：其中A代表：其中X是氢原子、卤原子或硝基基团，R.sup.1是--X.sup.1 Z.sup.1（X.sup.1是氧原子或硫原子，Z.sup.1是取代或未取代的烷基基团、取代或未取代的烯基基团、取代或未取代的炔基基团、取代或未取代的芳基基团或取代或未取代的杂芳基团）、--COZ.sup.1基团（Z.sup.1如上定义），##STR3##基团（Z.sup.1如上定义，Z.sup.2是--CO.sub.2 Z.sup.3，其中Z.sup.3与Z.sup.1相同，或--SO.sub.2 Z.sup.3，其中Z.sup.3如上定义，n为0或1），##STR4##（Z.sup.1和Z.sup.3如上定义）或##STR5##（X.sup.2、X.sup.3和X.sup.4分别为氧原子或硫原子，Z.sup.4和Z.sup.5与Z.sup.1相同），R.sup.3是硝基基团或##STR6##（R.sup.4和R.sup.5分别为烷基基团，或它们与相邻氮原子一起形成杂环基团），或##STR7##其中X和R.sup.3如上定义，R.sup.2是--X.sup.1 Z.sup.1（X.sup.1和Z.sup.1如上定义）；Y是卤原子、取代或未取代的烷基基团、取代或未取代的烷氧基团、取代或未取代的烷硫基团、硝基或##STR8##（R.sup.6和R.sup.7分别为取代或未取代的烷基基团）；R是##STR9##（R.sup.8与Y相同，q为1至4的整数），##STR10##（R.sup.8如上定义，r为1至3的整数）或##STR11##（R.sup.8和r如上定义）；m为1至4的整数，或其盐。
• Synthesis and Antitumor Activities of Novel Benzoylphenylurea Derivatives.
  作者：Hiroshi OKADA、Tohru KOYANAGI、Nobutoshi YAMDA、Takahiro HAGA

  DOI：10.1248/cpb.39.2308

  日期：——

  Seventy novel benzoylphenylurea compounds were synthesized and their antitumor activities were examined in vivo against P388 leukemia. N-(2-Nitrobenzoyl)-N'-[4-(2-pyrimidinyloxy)phenyl]ureas showed the highest antitumor activities when dosed intraperitoneally or orally. Their structure-activity relationships were examined with particular focus on the position and the variety of subsitituent on each aryl ring.

  合成了七十种新的苯甲酰苯基脲化合物，并对其在体内对P388白血病的抗肿瘤活性进行了研究。N-(2-硝基苯甲酰)-N'-[4-(2-吡啶基氧)苯基]脲在腹腔注射或口服给药时显示出最高的抗肿瘤活性。研究了它们的结构-活性关系，特别关注每个芳环上取代基的位置和种类。
• [EN] hTERT MODULATORS AND METHODS OF USE<br/>[FR] MODULATEURS HTERT ET PROCÉDÉS D'UTILISATION
  申请人：UNIV ARIZONA

  公开号：WO2017095969A1

  公开（公告）日：2017-06-08

  The present invention provides hTERT modulators and methods for producing and using the same. In particular, the present invention provide a compound of the formula as described herein. Some aspects of the invention are based on the characterization of the effect of hTERT core promoter region mutants on the 5-12 G-quadruplex structure and its stability. It is believed that some of the compounds of the invention bind selectively to the G-quadruplex in the hTERT core promoter mutant, which results in reversal of the effect of mutant promoter activation.

  本发明提供hTERT调节剂及其生产和使用方法。具体来说，本发明提供了如下所述的一种化合物。该发明的一些方面基于对hTERT核心启动子区域突变体对5-12 G-四链结构及其稳定性影响的表征。据信，本发明的一些化合物选择性地结合到hTERT核心启动子突变体中的G-四链结构，从而逆转突变启动子激活的效果。
• N-Benzoyl urea compounds, antitumorous compositions containing them, and process for their preparation
  申请人：ISHIHARA SANGYO KAISHA, LTD.

  公开号：EP0226104A2

  公开（公告）日：1987-06-24

  An N-benzoyl urea compound having the formula: wherein X is a hydrogen atom, a halogen atom or a nitro group, n is an integer of from 1 to 3, and Q is wherein Y, is an unsubstituted or substituted alkyl group, or an alkoxy or alkoxycarbonyl group with its alkyl moiety unsubstituted or substituted, Y2 is a hydrogen atom, a halogen atom, a nitro group, an unsubstituted or substituted alkyl group, or an alkoxy or alkoxycarbonyl group with its alkyl moiety unsubstituted or substituted, Z is a hydrogen atom, a halogen atom, a trifluoromethyl group or a nitro group, and each of A and B is =CH- or a nitrogen atom, provided that one of A and B is =CH- and the other is a nitrogen atom, with the provisos (1) that when Q is where when X is a hydrogen atom and Y, is an alkyl group, Z is not a hydrogen atom, a halogen atom nor a trifluoromethyl group, and (2) that when Q is wherein A is a nitrogen atom and Y, is a trifluoromethyl group, Y2 is other than a hydrogen atom.

  一种 N-苯甲酰基脲化合物，其式如下 其中 X 是氢原子、卤素原子或硝基，n 是 1 至 3 的整数，Q 是 其中 Y 是未取代或取代的烷基，或其烷基未取代或取代的烷氧基或烷氧羰基， Y2 是氢原子、卤素原子、硝基、未取代或取代的烷基、或烷氧基或烷氧基羰基，其烷基未被取代或取代，Z 是氢原子、卤素原子、三氟甲基或硝基，A 和 B 中的每一个是 =CH- 或氮原子，条件是 A 和 B 中的一个是 =CH-，另一个是氮原子，但书 (1) 当 Q 是 其中 X 为氢原子，Y 为烷基时，Z 不是氢原子、卤素原子或三氟甲基，以及 (2) 当 Q 为 其中 A 为氮原子，Y 为三氟甲基时，Y2 不是氢原子。
• Substituted benzene derivatives, processes for their production and antitumour compositions containing them
  申请人：ISHIHARA SANGYO KAISHA, LTD.

  公开号：EP0335408A2

  公开（公告）日：1989-10-04

  A substituted benzene derivative represented by a formula: where A represents: wherein X is a hydrogen atom, a halogen atom or a nitro group, R¹ is -X¹Z¹ (X¹ is an oxygen atom or a sulfur atom and Z¹ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substitute or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group), -COZ¹ group (Z¹ is as defined above), group (Z¹ is as defined above, Z² is -CO₂Z³ wherein Z³ is the same as Z¹, or -SO₂Z³ wherein Z³ is as defined above and n is 0 or 1), (Z¹ and Z³ are as defined above) or (X², X³ and X⁴ are, respectively, an oxygen atom or a sulfur atom and Z⁴ and Z⁵ are the same as Z¹), and R³ is a nitro group or (R⁴ and R⁵ are, respectively, an alkyl group, or they may form a heterocyclic group together with the adjacent nitrogen atom), or wherein X and R³ are as defined above and R² is -X¹Z¹ (X¹ and Z¹ are as defined above); Y is a halogen atom, a subsituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkythio group, a nitro group or (R⁶ and R⁷ are, respectively, a substituted or unsubstituted alkyl group); R is (R⁸ is the same as Y and q is an integer of 1 to 4), (R⁸ is as defined above, and r is an integer of 1 to 3) or (R⁸ and r are as defined above); and m is an integer of 1 to 4, or its salt.

  一种取代的苯衍生物，由式表示： 其中 A 代表 其中 X 是氢原子、卤素原子或硝基，R¹ 是-X¹Z¹（X¹ 是氧原子或硫原子，Z¹ 是取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳基或取代或未取代的杂芳基），-COZ¹ 基团（Z¹ 如上定义）、 基团（Z¹ 如上定义，Z² 为-CO₂Z³，其中 Z³ 与 Z¹ 相同，或-SO₂Z³，其中 Z³ 如上定义，且 n 为 0 或 1）、 (Z¹ 和 Z³ 如上定义）或 (X²、X³ 和 X⁴ 分别为氧原子或硫原子，且 Z⁴ 和 Z⁵ 与 Z¹ 相同），且 R³ 为硝基或 (R⁴ 和 R⁵ 分别为烷基，或可与相邻的氮原子一起形成杂环基团），或 其中 X 和 R³ 如上文所定义，R² 是-X¹Z¹（X¹ 和 Z¹ 如上文所定义）；Y 是卤素原子、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烷硫基、硝基，或 (R⁶ 和 R⁷ 分别是取代或未取代的烷基）； R 是 (R⁸ 与 Y 相同，q 为 1 至 4 的整数)、 (R⁸如上定义，且 r 为 1 至 3 的整数）或 (R⁸ 和 r 如上定义）；以及 m 是 1 至 4 的整数，或其盐。