(E)-3-[1-[2-(4-Methoxybenzylamino)-4-pyrimidinyl]-5-methyl-4-pyrazolyl]-2-propenal | 210992-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-[1-[2-(4-Methoxybenzylamino)-4-pyrimidinyl]-5-methyl-4-pyrazolyl]-2-propenal
• 英文别名: (E)-3-[1-[2-[(4-methoxyphenyl)methylamino]pyrimidin-4-yl]-5-methylpyrazol-4-yl]prop-2-enal
• CAS: 210992-74-8
• 化学式: C₁₉H₁₉N₅O₂
• 分子量: 349.392
• InChiKey: HLECALHWNVSYOI-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-[1-[2-(4-Methoxybenzylamino)-4-pyrimidinyl]-5-methyl-4-pyrazolyl]-2-propenal 在 sodium cyanoborohydride 、 溶剂黄146 、 苯甲醚 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-[1-(2-Amino-4-pyrimidinyl)-5-methyl-4-pyrazolyl]-3-[4-(3,5-difluorophenyl)-1-piperazinyl]-1-trans-propene Hydrochloride
  参考文献：
  名称：

  Synthesis and mechanism of action of novel pyrimidinyl pyrazole derivatives possessing antiproliferative activity

  摘要：

  Pyrimidinyl pyrazole derivatives 1-4, prepared as a new scaffold of an anti-tumor agent, showed antiproliferative activity against human lung cancer cell lines and inhibited tubulin polymerization. Furthermore, it was found that compound 2 bound at the colchicine site on tubulin, but the tubulin binding pattern was different from that of colchicine. Here, we describe the synthesis of the derivatives and the differences of the action mechanism on tubulin polymerization inhibition between compound 2 and colchicine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00568-1
• 作为产物：
  描述：

  Ethyl 1-[2-(4-Methoxybenzylamino)-4-pyrimidinyl]-5-methyl-4-pyrazolecarboxylate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 80.0h， 生成 (E)-3-[1-[2-(4-Methoxybenzylamino)-4-pyrimidinyl]-5-methyl-4-pyrazolyl]-2-propenal
  参考文献：
  名称：

  Synthesis and mechanism of action of novel pyrimidinyl pyrazole derivatives possessing antiproliferative activity

  摘要：

  Pyrimidinyl pyrazole derivatives 1-4, prepared as a new scaffold of an anti-tumor agent, showed antiproliferative activity against human lung cancer cell lines and inhibited tubulin polymerization. Furthermore, it was found that compound 2 bound at the colchicine site on tubulin, but the tubulin binding pattern was different from that of colchicine. Here, we describe the synthesis of the derivatives and the differences of the action mechanism on tubulin polymerization inhibition between compound 2 and colchicine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00568-1

文献信息

• PYRAZOLE DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1022270A1

  公开（公告）日：2000-07-26

  A compound represented by formula (I) or a salt thereof; wherein R1 and R2, which may be the same or different, each represent a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, an amino group, an alkylamino group, an aryl group or an alkyl group; R3 and R4, which may be the same, or different, each represent a hydrogen atom, a halogen atom, an alkoxy group, an amino group, an alkylamino group, an aryl group or an alkyl group; R5 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or an arylalkyl group; Q represents an amidino group, a cycloalkyl group, a phenyl group or amonocyclic heterocyclic group except a pyrimidinyl group bonded to the N atom at its 2-position; G represents a nitrogen-containing saturated heterocyclic structure represented by formula: wherein X1 represents a nitrogen atom or CH, in which the ring may have a keto group and may have one or more substituents; Z represents a phenyl or heterocyclic group which may have one or more substituents, in which two substituents on the phenyl or heterocyclic group may be connected to each other to form a ring to provide a condensed bicyclic structure as a whole; the substituent on Z and the substituent on G may be connected to each other to form a condensed tricyclic or tetracyclic structure as a whole, and an antitumor agent containing the compound or a salt thereof as an active ingredient.

  式 (I) 所代表的化合物或其盐； 其中 R1 和 R2 可以相同或不同，各自代表氢原子、卤素原子、羟基、烷氧基、氨基、烷基氨基、芳基或烷基； R3 和 R4 可以相同或不同，各自代表氢原子、卤素原子、烷氧基、氨基、烷基氨基、芳基或烷基；R5 代表氢原子、烷基、烯基、炔基、芳基或芳烷基； Q 代表脒基、环烷基、苯基或胺环杂环基团，但在 2 位与 N 原子键合的嘧啶基除外； G 代表由式表示的含氮饱和杂环结构： 其中 X1 代表氮原子或 CH、 其中环可具有酮基，并可具有一个或多个取代基； Z代表苯基或杂环基团，可具有一个或多个取代基，其中苯基或杂环基团上的两个取代基可相互连接形成一个环，以提供一个整体的缩合双环结构；Z上的取代基和G上的取代基可以相互连接，形成一个缩合的三环或四环结构整体，以及含有该化合物或其盐作为活性成分的抗肿瘤剂。
• US6169086B1
  申请人：——

  公开号：US6169086B1

  公开（公告）日：2001-01-02
• US6552018B1
  申请人：——

  公开号：US6552018B1

  公开（公告）日：2003-04-22
• Synthesis and mechanism of action of novel pyrimidinyl pyrazole derivatives possessing antiproliferative activity
  作者：Hitoshi Ohki、Kenji Hirotani、Hiroyuki Naito、Satoru Ohsuki、Megumi Minami、Akio Ejima、Yukiko Koiso、Yuichi Hashimoto

  DOI：10.1016/s0960-894x(02)00568-1

  日期：2002.11

  Pyrimidinyl pyrazole derivatives 1-4, prepared as a new scaffold of an anti-tumor agent, showed antiproliferative activity against human lung cancer cell lines and inhibited tubulin polymerization. Furthermore, it was found that compound 2 bound at the colchicine site on tubulin, but the tubulin binding pattern was different from that of colchicine. Here, we describe the synthesis of the derivatives and the differences of the action mechanism on tubulin polymerization inhibition between compound 2 and colchicine. (C) 2002 Elsevier Science Ltd. All rights reserved.