(S)-benzyl 2-(prop-2-yn-1-ylcarbamoyl)pyrrolidine-1-carboxylate | 1092547-89-1

• 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: (S)-benzyl 2-(prop-2-yn-1-ylcarbamoyl)pyrrolidine-1-carboxylate
• 英文别名: benzyl (2S)-2-(prop-2-ynylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 1092547-89-1
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: CENILUCZPMCQHO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-(prop-2-yn-1-ylcarbamoyl)pyrrolidine-1-carboxylate 、 benzyl N-[(2R,3R,4R,5S,6S)-2-[(2R,3S,4R,5S)-2-(azidomethyl)-5-[(1R,2R,3S,5R,6S)-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-6-hydroxy-3,5-bis(phenylmethoxycarbonylamino)cyclohexyl]oxy-4-hydroxyoxolan-3-yl]oxy-4,5-dihydroxy-6-(phenylmethoxycarbonylaminomethyl)oxan-3-yl]carbamate 在 copper diacetate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.23h， 生成 C₈₇H₉₉N₁₁O₂₇
  参考文献：
  名称：

  Surprising Alteration of Antibacterial Activity of 5′′-Modified Neomycin against Resistant Bacteria

  摘要：

  A facile synthetic protocol for the production of neomycin B derivatives with various modifications at the 5 '' position has been developed. The structural activity relationship (SAR) against aminoglycoside resistant bacteria equipped with various aminoglycoside-modifying enzymes (AMEs) was investigated. Enzymatic and molecular modeling studies reveal that the superb substrate promiscuity of AMEs allows the resistant bacteria to cope with diverse structural modifications despite the observation that several derivatives show enhanced antibacterial activity compared to the parent neomycin. Surprisingly, when testing synthetic neomycin derivatives against other human pathogens, two leads exhibit prominent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) that are known to exert a high level of resistance against clinically used aminoglycosides. These findings can be extremely useful in developing new aminoglycoside antibiotics against resistant bacteria. Our result also suggests that. new biological and antimicrobial activities can be obtained by chemical modifications of old drugs.

  DOI：

  10.1021/jm800997s
• 作为产物：
  描述：

  N-Z-L-脯氨酸甲酯 、 炔丙胺 在 CAL-B (Candida antarctica lipase B) immobilized on an acrylic resin (Novozyme 435) 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 以68%的产率得到(S)-benzyl 2-(prop-2-yn-1-ylcarbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  三组分化学酶法合成酰胺连接的1,2,3-三唑

  摘要：

  固定在丙烯酸树脂（Novozyme®435）上的CAL-B（南极假丝酵母脂肪酶B）可平滑地催化带有炔丙基胺的炔丙基酰胺的甲酯的氨解。在同一反应容器中，这些炔丙基衍生物在Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）点击反应中连续良好地转化为酰胺连接的1,2,3-三唑，其收率良好。

  DOI：

  10.1016/j.tetlet.2013.06.051

文献信息

• Surprising Alteration of Antibacterial Activity of 5′′-Modified Neomycin against Resistant Bacteria
  作者：Jianjun Zhang、Fang-I. Chiang、Long Wu、Przemyslaw Greg Czyryca、Ding Li、Cheng-Wei Tom Chang

  DOI：10.1021/jm800997s

  日期：2008.12.11

  A facile synthetic protocol for the production of neomycin B derivatives with various modifications at the 5 '' position has been developed. The structural activity relationship (SAR) against aminoglycoside resistant bacteria equipped with various aminoglycoside-modifying enzymes (AMEs) was investigated. Enzymatic and molecular modeling studies reveal that the superb substrate promiscuity of AMEs allows the resistant bacteria to cope with diverse structural modifications despite the observation that several derivatives show enhanced antibacterial activity compared to the parent neomycin. Surprisingly, when testing synthetic neomycin derivatives against other human pathogens, two leads exhibit prominent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) that are known to exert a high level of resistance against clinically used aminoglycosides. These findings can be extremely useful in developing new aminoglycoside antibiotics against resistant bacteria. Our result also suggests that. new biological and antimicrobial activities can be obtained by chemical modifications of old drugs.
• Three-component chemoenzymatic synthesis of amide ligated 1,2,3-triazoles
  作者：Sidra Hassan、Roxanne Tschersich、Thomas J.J. Müller

  DOI：10.1016/j.tetlet.2013.06.051

  日期：2013.8

  CAL-B (Candida antarctica lipase B) immobilized on an acrylic resin (Novozyme® 435) smoothly catalyzes the aminolysis of methyl esters with propargyl amine furnishing propargyl amides. In the same reaction vessel these propargyl derivatives are consecutively transformed into amide ligated 1,2,3-triazoles in a Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction in good to excellent yields

  固定在丙烯酸树脂（Novozyme®435）上的CAL-B（南极假丝酵母脂肪酶B）可平滑地催化带有炔丙基胺的炔丙基酰胺的甲酯的氨解。在同一反应容器中，这些炔丙基衍生物在Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）点击反应中连续良好地转化为酰胺连接的1,2,3-三唑，其收率良好。