1-氨基-3-羟基胍 | 36778-67-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-氨基-3-羟基胍
• 英文名称: N-hydroxy-N'-amino guanidine
• 英文别名: N-Hydroxyhydrazinecarboximidamide；2-amino-1-hydroxyguanidine
• CAS: 36778-67-3
• 化学式: CH₆N₄O
• 分子量: 90.0848
• InChiKey: MYYGWTHTRXMJJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.7
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异香兰素 、 1-氨基-3-羟基胍 以 甲醇 为溶剂， 反应 3.0h， 以67%的产率得到1-(3-hydroxy-4-methoxybenzylideneamino)-3-hydroxy-guanidine
  参考文献：
  名称：

  N-Hydroxy-N′-aminoguanidines as anti-cancer lead molecule: QSAR, synthesis and biological evaluation

  摘要：

  The intrinsic pharmacophore model (r(pred)(2) and r(m)(2) of 0.858 and 0.725) has been developed and used as a query to screen in-house built library based on N-hydroxy-N'-aminoguanidine (HAG) analogs. The pharmacophoric modeled based HITs were synthesized and evaluated for anticancer activity and cytotoxicity. One of the compounds (15) appeared as promising lead candidate with an IC50 value of 11 mu M yielded in HL-60 promyelocytic leukemia cells. Compound 15 reveals significantly lower cytotoxicity against HeLa and Vero cell with CC50 values of more than 100 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.009
• 作为产物：
  描述：

  1-氨基-2-甲基异硫代脲 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以70%的产率得到1-氨基-3-羟基胍
  参考文献：
  名称：

  N-Hydroxy-N′-aminoguanidines as anti-cancer lead molecule: QSAR, synthesis and biological evaluation

  摘要：

  The intrinsic pharmacophore model (r(pred)(2) and r(m)(2) of 0.858 and 0.725) has been developed and used as a query to screen in-house built library based on N-hydroxy-N'-aminoguanidine (HAG) analogs. The pharmacophoric modeled based HITs were synthesized and evaluated for anticancer activity and cytotoxicity. One of the compounds (15) appeared as promising lead candidate with an IC50 value of 11 mu M yielded in HL-60 promyelocytic leukemia cells. Compound 15 reveals significantly lower cytotoxicity against HeLa and Vero cell with CC50 values of more than 100 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.009

文献信息

• Chemical scaffolds with structural similarities to siderophores of nonribosomal peptide–polyketide origin as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis
  作者：Julian A. Ferreras、Akash Gupta、Neal D. Amin、Arijit Basu、Barij N. Sinha、Stefan Worgall、Venkatesan Jayaprakash、Luis E.N. Quadri

  DOI：10.1016/j.bmcl.2011.08.052

  日期：2011.11

  Mycobacterium tuberculosis (Mtb) and Yersinia pestis (Yp) produce siderophores with scaffolds of nonribosomal peptide-polyketide origin. Compounds with structural similarities to these siderophores were synthesized and evaluated as antimicrobials against Mtb and Yp under iron-limiting conditions mimicking the iron scarcity these pathogens encounter in the host and under standard iron-rich conditions. Several new antimicrobials were identified, including some with increased potency in the iron-limiting condition. Our study illustrates the possibility of screening compound libraries in both iron-rich and iron-limiting conditions to identify antimicrobials that may selectively target iron scarcity-adapted bacteria and highlights the usefulness of building combinatorial libraries of compounds having scaffolds with structural similarities to siderophores to feed into antimicrobial screening programs. Published by Elsevier Ltd.
• N-Hydroxy-N′-aminoguanidines as anti-cancer lead molecule: QSAR, synthesis and biological evaluation
  作者：Arijit Basu、Barij N. Sinha、Philipp Saiko、Geraldine Graser、Thomas Szekeres

  DOI：10.1016/j.bmcl.2011.04.009

  日期：2011.6

  The intrinsic pharmacophore model (r(pred)(2) and r(m)(2) of 0.858 and 0.725) has been developed and used as a query to screen in-house built library based on N-hydroxy-N'-aminoguanidine (HAG) analogs. The pharmacophoric modeled based HITs were synthesized and evaluated for anticancer activity and cytotoxicity. One of the compounds (15) appeared as promising lead candidate with an IC50 value of 11 mu M yielded in HL-60 promyelocytic leukemia cells. Compound 15 reveals significantly lower cytotoxicity against HeLa and Vero cell with CC50 values of more than 100 mu M. (C) 2011 Elsevier Ltd. All rights reserved.