tert-butyl 1-benzyl-2-oxopyrrolidin-3-ylcarbamate | 92235-37-5

• 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: tert-butyl 1-benzyl-2-oxopyrrolidin-3-ylcarbamate
• 英文别名: (3S)-3-(N-BOC-amino)-1-benzylazolan-2-one；tert-butyl N-[(3S)-1-benzyl-2-oxopyrrolidin-3-yl]carbamate
• CAS: 92235-37-5
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: LZJJJIXRYPMHBM-ZDUSSCGKSA-N

物化性质

• 沸点：
  477.5±44.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  tert-butyl 1-benzyl-2-oxopyrrolidin-3-ylcarbamate 在 盐酸 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.25h， 生成 4-{5-[(1-Benzyl-2-oxo-pyrrolidin-3-ylamino)-methyl]-imidazol-1-ylmethyl}-benzonitrile
  参考文献：
  名称：

  Design and Biological Activity of (S)-4-(5-{[1-(3-Chlorobenzyl)-2- oxopyrrolidin-3-ylamino]methyl}imidazol-1-ylmethyl)benzonitrile, a 3-Aminopyrrolidinone Farnesyltransferase Inhibitor with Excellent Cell Potency

  摘要：

  The synthesis, structure-activity relationships, and biological properties of a novel series of imidazole-containing inhibitors of farnesyltransferase are described. Starting from a 3-amino-pyrrolidinone core, a systematic series of modifications provided 5h, a non-thiol, non-peptide farnesyltransferase inhibitor with excellent bioavailability in dogs. Compound 5h was found to have an unusually favorable ratio of cell potency to intrinsic potency, compared with other known FTIs. It exhibited excellent potency against a range of tumor cell lines in vitro and showed full efficacy in the K-rasB transgenic mouse model.

  DOI：

  10.1021/jm010156p
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 N-甲基吗啉 、 sodium hydride 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.92h， 生成 tert-butyl 1-benzyl-2-oxopyrrolidin-3-ylcarbamate
  参考文献：
  名称：

  通过分子间炔-异氰酸酯点击反应中Spiro-2 H-吡咯的扩环取代吡咯内酰胺

  摘要：

  利用螺-2 H-吡咯（分子间炔烃-异氰酸酯点击反应的产物）的扩环反应，可以轻松合成6至8元的吡咯内酰胺。螺2 H-吡咯成功扩环成吡咯内酰胺的关键是内部烯烃和酰胺羰基之间通过构象锁定的双环结构之间的强制轨道重叠。新近公开的α-异氰基内酰胺，点击反应的底物，应在合成重要的药学上重要的杂环化合物中找到其效用。

  DOI：

  10.1021/acs.orglett.6b03786

文献信息

• [EN] NEW HETEROCYCLIC AMIDE COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX COMPOSES AMIDES HETEROCYCLIQUES UTILISES POUR LE TRAITEMENT D'AFFECTIONS INFLAMMATOIRES ET ALLERGIQUES; PROCEDE PERMETTANT DE LES FABRIQUER ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：GLENMARK PHARMACEUTICALS LTD

  公开号：WO2004022536A1

  公开（公告）日：2004-03-18

  The present invention relates to novel heterocyclic compounds that inhibit phosphodiesterase type 4 (PDE 4). The compounds are useful for treating inflammatory conditions, diseases of the central nervous systems and insulin resistant diabetes.

  本发明涉及一种新型杂环化合物，可抑制磷酸二酯酶4型（PDE 4）。这些化合物可用于治疗炎症性疾病、中枢神经系统疾病和胰岛素抵抗性糖尿病。
• Design and Biological Activity of (<i>S</i>)-4-(5-{[1-(3-Chlorobenzyl)-2- oxopyrrolidin-3-ylamino]methyl}imidazol-1-ylmethyl)benzonitrile, a 3-Aminopyrrolidinone Farnesyltransferase Inhibitor with Excellent Cell Potency
  作者：Ian M. Bell、Steven N. Gallicchio、Marc Abrams、Douglas C. Beshore、Carolyn A. Buser、J. Christopher Culberson、Joseph Davide、Michelle Ellis-Hutchings、Christine Fernandes、Jackson B. Gibbs、Samuel L. Graham、George D. Hartman、David C. Heimbrook、Carl F. Homnick、Joel R. Huff、Kelem Kassahun、Kenneth S. Koblan、Nancy E. Kohl、Robert B. Lobell、Joseph J. Lynch、Patricia A. Miller、Charles A. Omer、A. David Rodrigues、Eileen S. Walsh、Theresa M. Williams

  DOI：10.1021/jm010156p

  日期：2001.8.1

  The synthesis, structure-activity relationships, and biological properties of a novel series of imidazole-containing inhibitors of farnesyltransferase are described. Starting from a 3-amino-pyrrolidinone core, a systematic series of modifications provided 5h, a non-thiol, non-peptide farnesyltransferase inhibitor with excellent bioavailability in dogs. Compound 5h was found to have an unusually favorable ratio of cell potency to intrinsic potency, compared with other known FTIs. It exhibited excellent potency against a range of tumor cell lines in vitro and showed full efficacy in the K-rasB transgenic mouse model.
• Substituted Pyrrololactams via Ring Expansion of Spiro-2<i>H</i>-pyrroles from Intermolecular Alkyne–Isocyanide Click Reactions
  作者：Jimil George、Hun Young Kim、Kyungsoo Oh

  DOI：10.1021/acs.orglett.6b03786

  日期：2017.2.3

  The facile synthesis of 6- to 8-membered pyrrololactams has been developed using a ring expansion of spiro-2H-pyrroles, the products of intermolecular alkyne–isocyanide click reactions. The key to successful ring expansion of spiro-2H-pyrroles to pyrrololactams is the enforced orbital overlap between the internal alkene and the amide carbonyl group through the conformationally locked bicyclic structures

  利用螺-2 H-吡咯（分子间炔烃-异氰酸酯点击反应的产物）的扩环反应，可以轻松合成6至8元的吡咯内酰胺。螺2 H-吡咯成功扩环成吡咯内酰胺的关键是内部烯烃和酰胺羰基之间通过构象锁定的双环结构之间的强制轨道重叠。新近公开的α-异氰基内酰胺，点击反应的底物，应在合成重要的药学上重要的杂环化合物中找到其效用。