甲氧基(4-甲氧基苯基)亚甲基]丙二腈 | 5515-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 甲氧基(4-甲氧基苯基)亚甲基]丙二腈
• 英文名称: 2-[methoxy(4-methoxyphenyl)methylidene]propanedinitrile
• 英文别名: p-Methoxyphenylmethoxymethylenmalononitril；2-Cyan-3-methoxy-3-<4-methoxy-phenyl>-acrylonitril；Propanedinitrile, [methoxy(4-methoxyphenyl)methylene]-；2-[methoxy-(4-methoxyphenyl)methylidene]propanedinitrile
• CAS: 5515-13-9
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: AGRLVQLFYRSJOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  甲氧基(4-甲氧基苯基)亚甲基]丙二腈 在 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 16.0h， 生成 1-(2-chloro-2-phenylethyl)-3-(4-methyoxyphenyl)-1H-pyrazolo-[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Studies on the ATP Binding Site of Fyn Kinase for the Identification of New Inhibitors and Their Evaluation as Potential Agents against Tauopathies and Tumors

  摘要：

  Fyn is a member of the Src-family of nonreceptor protein-tyrosine kinases. Its abnormal activity has been shown to be related to various human cancers as well as to severe pathologies,; such as Alzheimer's and Parkinson's diseases. Herein, a structure-based drug design protocol was employed aimed at identifying novel Fyn inhibitors. Two hits from commercial sources (1, 2) were found active against Fyn with K-i of about 2 mu M, while derivative 4a, derived from our internal library, showed a K-i of 0.9 mu M. A hit-to-lead optimization effort was then initiated on derivative 4a to improve its potency. Slightly modifications rapidly determine an increase in the binding affinity, with the best inhibitors 4c and 44 having K(i)s of 70 and 95 nM, respectively. Both compounds were found able to inhibit the phosphorylation of : the protein Tau in an Alzheimer's model cell line and showed antiproliferative activities against different cancer cell lines.

  DOI：

  10.1021/acs.jmedchem.5b00140
• 作为产物：
  描述：

  大茴香酸 在 氯化亚砜 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 甲氧基(4-甲氧基苯基)亚甲基]丙二腈
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of 5-Amino-1H-pyrazole-4- carboxamide Derivatives as Potential Antitumor Agents

  摘要：

  已发现腺苷脱氨酶（ADA）抑制剂具有抗肿瘤活性。本文设计、合成了 13 种潜在的腺苷脱氨酶抑制剂 5-氨基-1H-吡唑-4-甲酰胺衍生物，并对其进行了抗肿瘤活性筛选。与其他 5-氨基-1H-吡唑-4-甲酰胺衍生物相比，化合物 8e 对雌激素受体阳性的乳腺癌细胞（MCF-7）具有很强的生长抑制作用和选择性。 此外，它还表现出适当的（μM）腺苷脱氨酶抑制效力。初步的结构-活性关系表明，在吡唑分子的氮原子上加入长链分支是这些衍生物具有活性的原因。

  DOI：

  10.2174/1570180811666140115234123

文献信息

• Preparation of 4,6-diaminopyrazolo[3,4-<i>d</i>] pyrimidines with variations in substitution at the 1- and 3-positions
  作者：Philip L. Southwick、Balram Dhawan

  DOI：10.1002/jhet.5570120621

  日期：1975.12

  of new derivatives of 4,6-diaminopyrazolo[3,4-d]pyrimidines substituted in the 1- and/or 3-positions have been obtained from reactions of guanidine carbonate with 1- and/or 3-substituted-5-amino-4-cyanopyrazoles. Use of triethanolamine as a reaction medium permitted preparation of certain derivatives which could not be obtained from the previously described fusion procedure. Some derivatives of 4-aminopyrazolo[3

  从碳酸胍与1-和/或3-取代的-5-的反应中获得了许多在1-和/或3-位被取代的4,6-二氨基吡唑并[3,4- d ]嘧啶的新衍生物。氨基-4-氰基吡唑。使用三乙醇胺作为反应介质允许制备某些衍生物，这些衍生物不能从前述的融合方法中获得。还从甲酰胺与相同的5-氨基-4-氰基吡唑的反应中获得了在1-和/或3-位被取代的4-氨基吡唑并[3，4- d ]嘧啶的一些衍生物。筛选了新化合物的体内抗疟活性，但发现它们没有活性。
• Libis,B.; Fleury,J.-P., Bulletin de la Societe Chimique de France, 1965, p. 3323 - 3329
  作者：Libis,B.、Fleury,J.-P.

  DOI：——

  日期：——
• Pyrrole derivatives as potent inhibitors of lymphocyte-specific kinase: Structure, synthesis, and SAR
  作者：Tetsuo Takayama、Hiroki Umemiya、Hideaki Amada、Tetsuya Yabuuchi、Fumiyasu Shiozawa、Hironori Katakai、Akiko Takaoka、Akie Yamaguchi、Mayumi Endo、Masakazu Sato

  DOI：10.1016/j.bmcl.2009.11.014

  日期：2010.1

  We have described the synthesis, enzyme inhibitory activity, structure-activity relationships, and proposed binding mode of a novel series of pyrrole derivatives as lymphocyte-specific kinase (Lck) inhibitors. The most potent analogs exhibited good enzyme inhibitory activity (IC(50)s <10 nM) for Lck kinase inhibition. (C) 2009 Elsevier Ltd. All rights reserved.
• One-pot synthesis of tetrasubstituted pyrazoles—proof of regiochemistry
  作者：Ulf Hanefeld、Charles W. Rees、Andrew J. P. White、David J. Williams

  DOI：10.1039/p19960001545

  日期：——

  1-Alkyl-5-amino-3-aryl-4-cyanopyrazoles, useful intermediates for fused heterocyclic systems, are synthesised by a one-pot three-step procedure from acid chlorides, malononitrile and alkylhydrazines, The regiochemistry of the hydrazine incorporation was proved in each case by X-ray crystallography and NMR spectroscopy.
• Synthesis of 6-Alkoxy-2-amino-5-cyanopyrimidines through Sodium Alkoxide-Induced Regiospecific Cyclization of 1,3-Dicarbonitriles
  作者：Miguel A. Perez、José L. Soto

  DOI：10.1055/s-1981-29654

  日期：——