1-(3,4-dimethoxybenzyl)guanidine hemisulfate | 19893-56-2

• 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: 1-(3,4-dimethoxybenzyl)guanidine hemisulfate
• 英文别名: Sulfuric acid--N-[(3,4-dimethoxyphenyl)methyl]guanidine (1/1)；2-[(3,4-dimethoxyphenyl)methyl]guanidine;sulfuric acid
• CAS: 19893-56-2
• 化学式: 2C₁₀H₁₅N₃O₂*H₂O₄S
• 分子量: 516.575
• InChiKey: UVZQAUJJKCITGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  175
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxybenzyl)guanidine hemisulfate 、 2,3-dihydro-3-dimethylaminomethylenethiopyrano[2,3-b]pyridin-4(4H)-one 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 6.25h， 以35%的产率得到2-N-(3,4-dimethoxybenzylamino)-5H-pyrido[3',2':5,6]thiopyrano[4,3-d]pyrimidine
  参考文献：
  名称：

  Discovery of Pyrido[3′,2′:5,6]thiopyrano[4,3-d]pyrimidine-Based Antiproliferative Multikinase Inhibitors

  摘要：

  Protein kinases dysregulation is extremely common in cancer cells, and the development of new agents able to simultaneously target multiple kinase pathways involved in angiogenesis and tumor growth may offer several advantages in the treatment of cancer. Herein we report the discovery of new pyridothiopyranopyrimidine derivatives (2-4) showing high potencies in VEGFR-2 KDR inhibition as well as antiproliferative effect on a panel of human tumor cell lines. Investigation on the selectivity profile of the representative 2-anilino-substituted compounds 3b, 3i, and 3j revealed a multiplicity of kinase targets that should account for the potent antiproliferative effect produced by these pyridothiopyranopyrimidine derivatives.

  DOI：

  10.1021/acsmedchemlett.8b00499
• 作为产物：
  描述：

  3,4-二甲氧基苄胺 、 S-甲基异硫脲硫酸盐 以 乙醇 、 水 为溶剂， 反应 18.0h， 以36%的产率得到1-(3,4-dimethoxybenzyl)guanidine hemisulfate
  参考文献：
  名称：

  Benzylguanidines and Other Galegine Analogues Inducing Weight Loss in Mice

  摘要：

  Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; +/- SEM) of -19.7 +/- 1.0, -11.0 +/- 0.7, and -7.3 +/- 0.8 in BALB/c, ob/ob, and DIO models, respectively.

  DOI：

  10.1021/jm8011933

文献信息

• Discovery of Pyrido[3′,2′:5,6]thiopyrano[4,3-<i>d</i>]pyrimidine-Based Antiproliferative Multikinase Inhibitors
  作者：Silvia Salerno、Elisabetta Barresi、Aída Nelly García-Argáez、Sabrina Taliani、Francesca Simorini、Giorgio Amendola、Stefano Tomassi、Sandro Cosconati、Ettore Novellino、Federico Da Settimo、Anna Maria Marini、Lisa Dalla Via

  DOI：10.1021/acsmedchemlett.8b00499

  日期：2019.4.11

  Protein kinases dysregulation is extremely common in cancer cells, and the development of new agents able to simultaneously target multiple kinase pathways involved in angiogenesis and tumor growth may offer several advantages in the treatment of cancer. Herein we report the discovery of new pyridothiopyranopyrimidine derivatives (2-4) showing high potencies in VEGFR-2 KDR inhibition as well as antiproliferative effect on a panel of human tumor cell lines. Investigation on the selectivity profile of the representative 2-anilino-substituted compounds 3b, 3i, and 3j revealed a multiplicity of kinase targets that should account for the potent antiproliferative effect produced by these pyridothiopyranopyrimidine derivatives.
• Benzylguanidines and Other Galegine Analogues Inducing Weight Loss in Mice
  作者：Geoffrey D. Coxon、Brian L. Furman、Alan L. Harvey、John McTavish、Mark H. Mooney、Mahmoud Arastoo、Alan R. Kennedy、Justice M. Tettey、Roger D. Waigh

  DOI：10.1021/jm8011933

  日期：2009.6.11

  Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; +/- SEM) of -19.7 +/- 1.0, -11.0 +/- 0.7, and -7.3 +/- 0.8 in BALB/c, ob/ob, and DIO models, respectively.