5-[1-(3,4,5-trimethoxy-phenyl)-vinyl]-pyrimidine-2,4-diamine | 184006-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[1-(3,4,5-trimethoxy-phenyl)-vinyl]-pyrimidine-2,4-diamine
• 英文别名: 5-[1-(3,4,5-Trimethoxyphenyl)ethenyl]pyrimidine-2,4-diamine
• CAS: 184006-40-4
• 化学式: C₁₅H₁₈N₄O₃
• 分子量: 302.333
• InChiKey: QDYWFBAEZOKVKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[1-(3,4,5-trimethoxy-phenyl)-vinyl]-pyrimidine-2,4-diamine 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 生成 5-[1-(3,4,5-trimethoxy-phenyl)-ethyl]-pyrimidine-2,4-diamine
  参考文献：
  名称：

  Analysis of complexes of inhibitors with Cryptosporidium hominis DHFR leads to a new trimethoprim derivative

  摘要：

  Cryptosporidiosis, an opportunistic infection affecting immunocompromised patients, the elderly, and children, is still an untreatable disease since the causative agent, Cryptosporidium hominis, is essentially resistant to all clinically used antimicrobial agents. In order to accelerate the design of new potent and selective inhibitors targeting dihydrofolate reductase of C. hominis (ChDHFR), we determined the structural basis for the potency of existing DHFR inhibitors using superpositions of the structure of ChDHFR with other species and analysis of active site complexes of ChDHFR bound to ligands exhibiting a wide range of IC50 values. This information was used to develop an accurate docking model capable of identifying potent inhibitors in silico. A series of C7-trimethoprim derivatives, designed to exploit a unique pocket in ChDHFR, was synthesized and evaluated; 7-ethyl TMP has four times higher activity than TMP against ChDHFR. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.047
• 作为产物：
  描述：

  甲氧苄啶 在 manganese(IV) oxide 、 三氟乙酸 作用下， 生成 5-[1-(3,4,5-trimethoxy-phenyl)-vinyl]-pyrimidine-2,4-diamine
  参考文献：
  名称：

  Analysis of complexes of inhibitors with Cryptosporidium hominis DHFR leads to a new trimethoprim derivative

  摘要：

  Cryptosporidiosis, an opportunistic infection affecting immunocompromised patients, the elderly, and children, is still an untreatable disease since the causative agent, Cryptosporidium hominis, is essentially resistant to all clinically used antimicrobial agents. In order to accelerate the design of new potent and selective inhibitors targeting dihydrofolate reductase of C. hominis (ChDHFR), we determined the structural basis for the potency of existing DHFR inhibitors using superpositions of the structure of ChDHFR with other species and analysis of active site complexes of ChDHFR bound to ligands exhibiting a wide range of IC50 values. This information was used to develop an accurate docking model capable of identifying potent inhibitors in silico. A series of C7-trimethoprim derivatives, designed to exploit a unique pocket in ChDHFR, was synthesized and evaluated; 7-ethyl TMP has four times higher activity than TMP against ChDHFR. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.047

文献信息

• [EN] ISO CA-4 AND ANALOGUES THEREOF AS POTENT CYTOTOXIC AGENTS INHIBITING TUBULINE POLYMERISATION<br/>[FR] ISO CA-4 ET ANALOGUES : PUISSANTS CYTOTOXIQUES, INHIBITEURS DE LA POLYMERISATION DE LA TUBULINE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2008122620A1

  公开（公告）日：2008-10-16

  [EN] The invention relates to a compound of the formula (I) in which: R₁, R₂ and R₃ are independently a methoxy group optionally substituted by one or more fluorine atoms; R₄ is a hydrogen atom; R₅ and R₆ are identical and each represent a hydrogen or fluorine atom; A is a cycle selected from the group including aryl and heteroaryl groups, wherein said groups can be substituted.
  [FR] Composé de formule (I) dans laquelle : R₁, R₂ et R₃ représentent, indépendamment les uns des autres, un groupe méthoxy éventuellement substitué par un ou plusieurs atomes de fluor; R₄ représente un atome d'hydrogène; R₅ et R₆ sont identiques et représentent chacun un atome d'hydrogène ou un atome de fluor; A est un cycle choisi dans le groupe comprenant les groupes aryles et hétéroaryles, lesdits groupes pouvant être substitués.