2-[(3-氯-苯基)-甲氧基-亚甲基]-丙二腈 | 81066-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(3-氯-苯基)-甲氧基-亚甲基]-丙二腈
• 英文名称: 2-[(3-Chlorophenyl)-methoxymethylidene]propanedinitrile
• CAS: 81066-92-4
• 化学式: C₁₁H₇ClN₂O
• 分子量: 218.642
• InChiKey: NBGDOTGLJHBTGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

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

  Identification of a new family of pyrazolo[3,4-d]pyrimidine derivatives as multitarget Fyn-Blk-Lyn inhibitors active on B- and T-lymphoma cell lines

  摘要：

  Abnormal activation of B-cell receptor (BCR) signaling plays a key role in the development of lymphoid malignancies, and could be reverted by the simultaneous inhibition of Lyn, Fyn and Blk, three members of the Src family kinase (SFK).Fyn and Blk are also promising targets for the treatment of some forms of T-cell non-Hodgkin lymphoma which point to the druggability of SFKs for the treatment of these cancers. We recently identified Si308 as a potent Fyn inhibitor, while preliminary data showed that it might also inhibit Lyn and Blk. Here, molecular modelling studies were coupled with enzymatic assays to further investigate the effect of Si308 on Lyn and Blk. A small library of pyrazolo[3,4-d]pyrimidines structurally related to Si308 was synthesized and tested on human lymphoma cell lines. Compound 2h emerged as a new multitarget inhibitor of Lyn, Fyn and Blk endowed with remarkable antiproliferative effects on human B and T lymphoma cell lines. Its favorable ADME properties make the compound suitable for further developments. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.07.048
• 作为产物：
  描述：

  3-氯苯甲酰氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.0h， 生成 2-[(3-氯-苯基)-甲氧基-亚甲基]-丙二腈
  参考文献：
  名称：

  Identification of a new family of pyrazolo[3,4-d]pyrimidine derivatives as multitarget Fyn-Blk-Lyn inhibitors active on B- and T-lymphoma cell lines

  摘要：

  Abnormal activation of B-cell receptor (BCR) signaling plays a key role in the development of lymphoid malignancies, and could be reverted by the simultaneous inhibition of Lyn, Fyn and Blk, three members of the Src family kinase (SFK).Fyn and Blk are also promising targets for the treatment of some forms of T-cell non-Hodgkin lymphoma which point to the druggability of SFKs for the treatment of these cancers. We recently identified Si308 as a potent Fyn inhibitor, while preliminary data showed that it might also inhibit Lyn and Blk. Here, molecular modelling studies were coupled with enzymatic assays to further investigate the effect of Si308 on Lyn and Blk. A small library of pyrazolo[3,4-d]pyrimidines structurally related to Si308 was synthesized and tested on human lymphoma cell lines. Compound 2h emerged as a new multitarget inhibitor of Lyn, Fyn and Blk endowed with remarkable antiproliferative effects on human B and T lymphoma cell lines. Its favorable ADME properties make the compound suitable for further developments. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.07.048

文献信息

• Lorente, A.; Navio, J. L. Garcia; Vaquero, J. J., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 49 - 51
  作者：Lorente, A.、Navio, J. L. Garcia、Vaquero, J. J.、Soto, J. L.

  DOI：——

  日期：——
• 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：——
• Synthesis of Heterocyclic Compounds; XL. Regioselective Synthesis of 4-Substituted 2-Amino-5-cyano-6-methoxy-3-benzenesulfonylpyridines
  作者：L. Fuentes、J. J. Vaquero、M. I. Ardid、J. C. Del Castillo、José L. Soto

  DOI：10.1055/s-1984-30965

  日期：——
• PEREZ, M. A.;SOTO, J. L., SYNTHESIS, BRD, 1981, N 12, 955-958
  作者：PEREZ, M. A.、SOTO, J. L.

  DOI：——

  日期：——