tert-butyl N-[(2S)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate | 1270202-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl N-[(2S)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
• CAS: 1270202-32-8
• 化学式: C₂₈H₃₁FN₄O₄
• 分子量: 506.577
• InChiKey: IUSWBYQNYUSDFV-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate 在 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 C₃₀H₂₇F₂N₅O₃
  参考文献：
  名称：

  Synthesis of uriedo and thiouriedo derivatives of peptide conjugated heterocycles – A new class of promising antimicrobials

  摘要：

  Forty five new derivatives of ureas and thioureas were synthesized by the reaction of peptide conjugated heterocycles with isocyanates and isothiocyanates respectively. All the compounds have been characterized by IR, H-1 NMR, mass and elemental analysis. The compounds were evaluated for their ability to inhibit the growth of a panel of microorganisms and all the synthesized compounds displayed an excellent antimicrobial activity. From structure-activity relationship studies, it was apparent that thioureas infact is slightly more active than ureas. Also, substituents on the phenyl ring of the title compounds play a key role in the activity. Further, compound 40 is nearly twenty times more potent than the standard used. These results present a platform for the further studies in this line. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.012
• 作为产物：
  描述：

  N-叔丁氧羰基-L-色氨酸 、 6-氟-3-哌啶-4-基-1,2-苯并异唑盐酸盐 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以96%的产率得到tert-butyl N-[(2S)-1-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials – A novel approach to enhance biocompatibility

  摘要：

  The peptides of elastin sequences chosen for the present study included tetrapeptides, pentapeptides and tricosapeptides (30 amino acids), synthesized by classical solution phase method and conjugated to [3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole]. The structures of the compounds were confirmed by physical and spectroscopic techniques followed by the antimicrobial evaluation by both agar well diffusion and microdilution methods. Here we wish to report the effect of conjugation of these moieties which enabled us to identify a novel set of peptides conjugated to heterocycle which have exhibited more potent antimicrobial activity than the conventional drugs used. Further, conjugates of tricosamers 34 and 35 were able to inhibit the growth of fungal species at 3-5 mu g/mL which is nearly 5 fold more potent than the reference drug. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.005

文献信息

• Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials – A novel approach to enhance biocompatibility
  作者：R. Suhas、S. Chandrashekar、D. Channe Gowda

  DOI：10.1016/j.ejmech.2010.12.005

  日期：2011.2

  The peptides of elastin sequences chosen for the present study included tetrapeptides, pentapeptides and tricosapeptides (30 amino acids), synthesized by classical solution phase method and conjugated to [3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole]. The structures of the compounds were confirmed by physical and spectroscopic techniques followed by the antimicrobial evaluation by both agar well diffusion and microdilution methods. Here we wish to report the effect of conjugation of these moieties which enabled us to identify a novel set of peptides conjugated to heterocycle which have exhibited more potent antimicrobial activity than the conventional drugs used. Further, conjugates of tricosamers 34 and 35 were able to inhibit the growth of fungal species at 3-5 mu g/mL which is nearly 5 fold more potent than the reference drug. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis of uriedo and thiouriedo derivatives of peptide conjugated heterocycles – A new class of promising antimicrobials
  作者：R. Suhas、S. Chandrashekar、D. Channe Gowda

  DOI：10.1016/j.ejmech.2011.12.012

  日期：2012.2

  Forty five new derivatives of ureas and thioureas were synthesized by the reaction of peptide conjugated heterocycles with isocyanates and isothiocyanates respectively. All the compounds have been characterized by IR, H-1 NMR, mass and elemental analysis. The compounds were evaluated for their ability to inhibit the growth of a panel of microorganisms and all the synthesized compounds displayed an excellent antimicrobial activity. From structure-activity relationship studies, it was apparent that thioureas infact is slightly more active than ureas. Also, substituents on the phenyl ring of the title compounds play a key role in the activity. Further, compound 40 is nearly twenty times more potent than the standard used. These results present a platform for the further studies in this line. (C) 2011 Elsevier Masson SAS. All rights reserved.