2.6-Dichlor-4.8-dianilino-pyrimido<5.4-d>pyrimidin | 93819-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2.6-Dichlor-4.8-dianilino-pyrimido<5.4-d>pyrimidin
• 英文别名: 2,6-dichloro-N,N'-diphenyl-pyrimido[5,4-d]pyrimidine-4,8-diamine；2,6-dichloro-N⁴,N⁸-diphenyl-pyrimido[5,4-d]pyrimidine-4,8-diyldiamine；2,6-Dichlor-N⁴,N⁸-diphenyl-pyrimido[5,4-d]pyrimidin-4,8-diyldiamin；2,6-Dichloro-N~4~,N~8~-diphenylpyrimido[5,4-d]pyrimidine-4,8-diamine；2,6-dichloro-4-N,8-N-diphenylpyrimido[5,4-d]pyrimidine-4,8-diamine
• CAS: 93819-72-8
• 化学式: C₁₈H₁₂Cl₂N₆
• 分子量: 383.239
• InChiKey: GXHYRYPQIXBOIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  C.I.酸性橙108 、 2.6-Dichlor-4.8-dianilino-pyrimido<5.4-d>pyrimidin 以 二甲基亚砜 为溶剂， 反应 6.0h， 以138 mg的产率得到2-({6-[(2-Hydroxyethyl)amino]-4,8-bis(phenylamino)pyrimido[5,4-d][1,3]diazin-2-yl}amino)ethan-1-ol
  参考文献：
  名称：

  Synthesis, Flow Cytometric Evaluation, and Identification of Highly Potent Dipyridamole Analogues as Equilibrative Nucleoside Transporter 1 Inhibitors

  摘要：

  Dipyridamole (Persantine) is a clinically used vasodilator with equilibrative nucleoside transporters I and 2 (ENT1 and ENT2) inhibitory activity albeit less potent than the prototype ENT1 inhibitor nitrobenzylmercaptopurine riboside (NBMPR). Dipyridamole is a good candidate for further exploration because it is a non-nucleoside and has a proven record of safe use in humans. A series of dipyridamole analogues were synthesized with systematic modification and evaluated as ENT1 inhibitors by flow cytometry. Compounds with much higher potency were identified, the best being 2,6-bis(diethanolamino)-4,8-diheptamethylene-iminopyrimido[5,4-d]pyrimidine (13) with a K-i of 0.49 nM compared to a Ki of 308 nM for dipyridamole. Compound 13 is similar in potency to the prototype potent ENT1 inhibitor NBMPR (0.43 nM). For the first time, a dipyridamole analogue has been identified that is equipotent with NBMPR. The SAR indicated that diethanolamine substituted analogues were more active than monoethanolamine compounds. Also, free hydroxyl groups are not essential for activity.

  DOI：

  10.1021/jm070311l
• 作为产物：
  描述：

  2,4,6,8-四氯嘧啶并[5,4-d]嘧啶 、 苯胺 以 四氢呋喃 为溶剂， 生成 2.6-Dichlor-4.8-dianilino-pyrimido<5.4-d>pyrimidin
  参考文献：
  名称：

  Synthesis, Flow Cytometric Evaluation, and Identification of Highly Potent Dipyridamole Analogues as Equilibrative Nucleoside Transporter 1 Inhibitors

  摘要：

  Dipyridamole (Persantine) is a clinically used vasodilator with equilibrative nucleoside transporters I and 2 (ENT1 and ENT2) inhibitory activity albeit less potent than the prototype ENT1 inhibitor nitrobenzylmercaptopurine riboside (NBMPR). Dipyridamole is a good candidate for further exploration because it is a non-nucleoside and has a proven record of safe use in humans. A series of dipyridamole analogues were synthesized with systematic modification and evaluated as ENT1 inhibitors by flow cytometry. Compounds with much higher potency were identified, the best being 2,6-bis(diethanolamino)-4,8-diheptamethylene-iminopyrimido[5,4-d]pyrimidine (13) with a K-i of 0.49 nM compared to a Ki of 308 nM for dipyridamole. Compound 13 is similar in potency to the prototype potent ENT1 inhibitor NBMPR (0.43 nM). For the first time, a dipyridamole analogue has been identified that is equipotent with NBMPR. The SAR indicated that diethanolamine substituted analogues were more active than monoethanolamine compounds. Also, free hydroxyl groups are not essential for activity.

  DOI：

  10.1021/jm070311l

文献信息

• Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides
  申请人：Cell Pathways, Inc.

  公开号：US06232312B1

  公开（公告）日：2001-05-15

  Combinations of substituted indenyl acetic acids and pyrimido-pyrimidine derivatives are useful in the treatment of colonic polyps and inhibiting the growth of neoplastic cells.

  取代基茚基乙酸和嘧啶并嘧啶衍生物的组合物在结肠息肉的治疗和抑制肿瘤细胞生长方面是有用的。
• Organic semiconductor materials using stacking-inducing compounds, compositions comprising such materials, organic semiconductor thin films formed using such compositions, and organic electronic devices incorporating such thin films
  申请人：Jeong Eun Jeong

  公开号：US20070287220A1

  公开（公告）日：2007-12-13

  Disclosed are organic semiconductor materials, including mixtures of relatively low molecular weight aromatic ring compounds, in which at least one nitrogen atom or oxygen atom is present as a heteroatom in the aromatic ring compounds for forming hydrogen bonds between the heteroatom(s) and adjacent molecules and thereby increase intermolecular stacking. Organic semiconductor layers formed using such organic semiconductor materials will, accordingly, exhibit increased intermolecular stacking and associated improvements in one or more electrical properties of the semiconductor layer. Organic thin film transistors incorporating such organic semiconductor layers will tend to exhibit improved transistor properties including, for example, increased carrier mobility and reduced off-state leakage current. Further, the organic semiconductor layers may be manufactured using conventional room temperature processes, for example, spin coating or printing, thereby simplifying the fabrication process.

  本发明涉及有机半导体材料，包括相对较低分子量的芳香环化合物混合物，其中至少一个氮原子或氧原子存在于芳香环化合物中，以形成氢键在杂原子和相邻分子之间，从而增加分子间堆积。因此，使用这种有机半导体材料形成的有机半导体层将表现出增加的分子间堆积和相关电性能的改善。包含这种有机半导体层的有机薄膜晶体管将倾向于表现出改进的晶体管特性，例如增加的载流子迁移率和减少的关断漏电流。此外，这种有机半导体层可以使用传统的室温工艺制造，例如旋涂或印刷，从而简化制造过程。
• GB807826
  申请人：——

  公开号：——

  公开（公告）日：——
• Substituted pyrimido-[5, 4-d]-pyrimidines
  申请人：THOMAE GMBH DR K

  公开号：US03031450A1

  公开（公告）日：1962-04-24
• US6232312B1
  申请人：——

  公开号：US6232312B1

  公开（公告）日：2001-05-15