2-amino-6-(methylthio)-4-morpholino-5-pyrimidinecarbonitrile | 136062-61-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-6-(methylthio)-4-morpholino-5-pyrimidinecarbonitrile
• 英文别名: 2-amino-4-morpholino-6-methylthio-5-pyrimidinecarbonitrile；2-Amino-4-methylsulfanyl-6-morpholin-4-ylpyrimidine-5-carbonitrile
• CAS: 136062-61-8
• 化学式: C₁₀H₁₃N₅OS
• 分子量: 251.312
• InChiKey: SOYRDQJLLCVGAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-6-(methylthio)-4-morpholino-5-pyrimidinecarbonitrile 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-Amino-4-[N'-but-(E)-ylidene-hydrazino]-6-morpholin-4-yl-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and in vitro antitumoral activity of new hydrazinopyrimidine-5-carbonitrile derivatives

  摘要：

  A new series of 2-amino-6-(2-alkyl or arylidenehydrazinyl)-4-(dialkylamino)pyrimidine-5-carbonitriles, 5-24, were synthesized in satisfactory overall yield, using 2-amino-4-(dialkylamino)-6-hydrazino-5-pyrimidinecarbonitriles 3, 4, as key intermediates, by applying classical synthetic methods to construct the hydrazone moiety at C-6 of the pyrimidine ring. Hydrazinopyrimidine derivatives 5-24 were evaluated for their in vitro anticancer activity toward cell lines of nine different types of human cancers. Some of the newly prepared compounds demonstrated inhibitory effects on the growth of a wide range of cancer cell lines generally at 10(-5) M level and in some cases at 10(-7) M concentrations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.012
• 作为产物：
  描述：

  3-amino-3-morpholinopropenenitrile 、 N-氰亚胺基-S,S-二硫代碳酸二甲酯 在 potassium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 2-amino-6-(methylthio)-4-morpholino-5-pyrimidinecarbonitrile
  参考文献：
  名称：

  Synthesis and in vitro antitumoral activity of new hydrazinopyrimidine-5-carbonitrile derivatives

  摘要：

  A new series of 2-amino-6-(2-alkyl or arylidenehydrazinyl)-4-(dialkylamino)pyrimidine-5-carbonitriles, 5-24, were synthesized in satisfactory overall yield, using 2-amino-4-(dialkylamino)-6-hydrazino-5-pyrimidinecarbonitriles 3, 4, as key intermediates, by applying classical synthetic methods to construct the hydrazone moiety at C-6 of the pyrimidine ring. Hydrazinopyrimidine derivatives 5-24 were evaluated for their in vitro anticancer activity toward cell lines of nine different types of human cancers. Some of the newly prepared compounds demonstrated inhibitory effects on the growth of a wide range of cancer cell lines generally at 10(-5) M level and in some cases at 10(-7) M concentrations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.012

文献信息

• Synthesis of 2-Amino-5-pyrimidinecarbonitrile Derivatives
  作者：Maria Teresa Cocco、Cenzo Congiu、Valentina Onnis、Antonio Maccioni

  DOI：10.1055/s-1991-26508

  日期：——

  2-Amino-4-dialkylamino- or -4-ethoxy-6-methylthio-5-pyrimidinecarbonitriles 3 are obtained through a base-induced reaction between 3-amino-3-(dialkylamino)propenenitriles 1 and N-[bis (methylthio)methylene] cyanamide (2).

  通过 3-氨基-3-(二烷基氨基)丙烯腈 1 和 N-[双（甲硫基）亚甲基]氰酰胺（2）之间的碱诱导反应，可获得 2-氨基-4-二烷基氨基-或-4-乙氧基-6-甲硫基-5-嘧啶甲腈 3。
• Transformation of 6-methylthiopyrimidines. Preparation of new pyrimidine derivatives and fused azolopyrimidines
  作者：Maria Teresa Cocco、Cenzo Congiu、Valentina Onnis

  DOI：10.1002/jhet.5570370406

  日期：2000.7

  6-benzylaminopyrimidine derivatives 2 and 4 respectively. The reaction of 1 with hydrazine hydrate, in ethanol, gave 6-hydrazino derivatives 6. However, by treating pyrimidines 1 in boiling hydrazine hydrate 3,6-diamino-4-hydrazino-1H-pyrazolo[3,4-d]pyrimidine 5 was obtained. The 6-hydrazinopyrimidines 6 could be converted into the pyrazolo[3,4-d], triazolo[4,3-c] and tetrazolo-[1,5-c]pyrimidines 7, 8 and 9 by

  2，4-二氨基-6-甲基硫代嘧啶1与甲氧基钠和苄胺反应，分别得到相应的6-甲氧基嘧啶和6-苄基氨基嘧啶衍生物2和4。1与水合肼在乙醇中的反应生成6-肼基衍生物6。但是，通过在沸腾水合肼3,6-二氨基-4-肼基-1 H-吡唑并[3,4- d ]嘧啶中处理嘧啶1获得5。可以将6-肼基嘧啶6转化为吡唑并[3,4- d ]，三唑并[4,3- c ]和四唑并-[1,5- c嘧啶7、8和9分别通过加热，原甲酸三甲酯和亚硝酸作用。