N, N′-di-Boc-N-but-2-enyl-S-methylisothiourea | 1176238-47-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N, N′-di-Boc-N-but-2-enyl-S-methylisothiourea
• 英文别名: N1,N2-bis(tert-butoxycarbonyl)-N1-(γ-methylallyl)-S-methylisothiourea；tert-butyl N-but-2-enyl-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-C-methylsulfanylcarbonimidoyl]carbamate
• CAS: 1176238-47-3
• 化学式: C₁₆H₂₈N₂O₄S
• 分子量: 344.475
• InChiKey: ZMOKIVMHIMEGCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  68.2
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N, N′-di-Boc-N-but-2-enyl-S-methylisothiourea 、 N-(8-氨基辛基)-1,8-辛烷二胺 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 以84%的产率得到1-amino-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(γ-methylallyl)guanidine)-9-azaheptadecane
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidino Compounds Endowed with Subnanomolar Affinity as Competitive Inhibitors of Maize Polyamine Oxidase

  摘要：

  Previous studies on agmatine and its derivatives suggested that the presence of hydrophobic groups on the guanidine moiety was a crucial key for inhibitory activity of maize polyamine oxidase. Accordingly, new lipophilic agmatine and iminoctadine derivatives were synthesized and tested for their ability to inhibit this enzyme. Several compounds showed an affinity in the nanomolar range, while a cyclopropylmethyl derivative of iminoctadine was found to be the most potent inhibitor of maize polyamine oxidase reported so far (K-i = 0.08 nM).

  DOI：

  10.1021/jm900371z
• 作为产物：
  描述：

  1-溴-2-丁烯 、 N,N'-bis-Boc-S-methyl-isothiourea 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 以70%的产率得到N, N′-di-Boc-N-but-2-enyl-S-methylisothiourea
  参考文献：
  名称：

  Synthesis of New Linear Guanidines and Macrocyclic Amidinourea Derivatives Endowed with High Antifungal Activity against Candida spp. and Aspergillus spp.

  摘要：

  New linear and Cyclic guanidines were synthesized and tested in vitro for their antifungal activity toward clinically relevant strains of Candida species, in comparison to fluconazole. Macrocyclic Compounds showed a minimum inhibitory concentration ill the micromolar range and a biological activity profile ill some cases better than that of fluconazole. One macrocyclic derivative was also tested against Aspergillus species and showed high antifungal activity comparable to that of amphotericin B and itraconazole.

  DOI：

  10.1021/jm900760k

文献信息

• Novel Macrocyclic Amidinoureas: Potent Non-Azole Antifungals Active against Wild-Type and Resistant Candida Species
  作者：Maurizio Sanguinetti、Stefania Sanfilippo、Daniele Castagnolo、Dominique Sanglard、Brunella Posteraro、Giovanni Donzellini、Maurizio Botta

  DOI：10.1021/ml400187w

  日期：2013.9.12

  Novel macrocyclic amidinourea derivatives 11, 18, and 25 were synthesized and evaluated as antifungal agents against wild-type and fluconazole resistant Candida species. Macrocyclic compounds 11 and 18 were synthesized through a convergent approach using as a key step a ring-closing metathesis macrocyclization reaction, whereas compounds 25 were obtained by our previously reported synthetic pathway. All the macrocyclic amidinoureas showed antifungal activity toward different Candida species higher or comparable to fluconazole and resulted highly active against fluconazole resistant Candida strains showing in many cases minimum inhibitory concentration values lower than voriconazole.