(+/-)-1-(carboxymethyl)-3-<(tert-butoxycarbonyl)amino>-2-piperidone | 733049-29-1

• 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: (+/-)-1-(carboxymethyl)-3-<(tert-butoxycarbonyl)amino>-2-piperidone
• 英文别名: 2-(3-((tert-butoxy)carbonylamino)-2-oxopiperidin-1-yl)acetic acid；2-(2-tert-butoxicarbonylamine-δ-valerolactam-N-yl)acetic acid；(3-tert-butoxycarbonylamino-2-oxopiperidin-1-yl)acetic acid；L-1-Carboxymethyl-3-tert butyloxycarbonylamino-2-piperidone；L-1-carboxymethyl-3-tert-butyloxycarbonylamino-2-piperidone；(+/-)-1-(carboxymethyl)-3-[(tert-butoxycarbonyl)amino]-2-piperidone；(3-[(Tert-butoxycarbonyl)amino]-2-oxopiperidin-1-YL)acetic acid；2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxopiperidin-1-yl]acetic acid
• CAS: 733049-29-1
• 化学式: C₁₂H₂₀N₂O₅
• 分子量: 272.301
• InChiKey: GLPLDJICXMMSBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(carboxymethyl)-3-<(tert-butoxycarbonyl)amino>-2-piperidone 在 palladium on activated charcoal N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S)-5-(diaminomethylideneamino)-2-[[2-[3-[[7-[[1-[2-[[(2S)-5-(diaminomethylideneamino)-1-methoxy-1-oxopentan-2-yl]amino]-2-oxoethyl]-2-oxopiperidin-3-yl]amino]-7-oxoheptanoyl]amino]-2-oxopiperidin-1-yl]acetyl]amino]pentanoate
  参考文献：
  名称：

  Design, synthesis and biological activity of a targeted library of potential tryptase inhibitors

  摘要：

  我们设计、合成并测试了两小类潜在的色氨酸酶抑制剂。第一类库由多种N取代的3-氨基哌啶-2-酮（6）组成，第二类（化合物7）是通过多样的碳链将化合物6在3-氨基功能上二聚化而制备的。我们已经建立了有效的路线，以便在溶液中和固体载体上获得化合物6。我们还比较了固相和溶液中的二聚化反应。四个化合物在1 µM的浓度下显示出较高的色氨酸酶抑制活性，但没有一个超过BABIM的色氨酸酶抑制活性。

  DOI：

  10.1039/b403629h
• 作为产物：
  描述：

  3-氨基-2-哌啶酮 在 palladium on activated charcoal 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 6.5h， 生成 (+/-)-1-(carboxymethyl)-3-<(tert-butoxycarbonyl)amino>-2-piperidone
  参考文献：
  名称：

  Conformationally restricted inhibitors of angiotensin-converting enzyme. Synthesis and computations

  摘要：

  A series of inhibitors of angiotensin converting enzyme (ACE, dipeptidyl carboxypeptidase, EC 3.4.15.1) is described which addresses certain conformational aspects of the enzyme-inhibitor interaction. In this study the alanylproline portion of the potent ACE inhibitor enalaprilat (2) is replaced by a series of monocyclic lactams containing the required recognition and binding elements. In order to more fully assess the lactam ring conformations and the key backbone angle psi as defined in 3 with respect to possible enzyme-bound conformations, a series of model lactams was investigated with use of molecular mechanics. The results point to a correlation between inhibitor potency (IC50) and the computed psi angle for the lowest energy conformation of the model compounds. Thus the psi angle as defined in 3 is an important determinant in the binding of inhibitors to ACE. The inhibition data in conjunction with the computational data have served to define a window of psi angles from 130 degrees to 170 degrees which seems to be acceptable to the ACE active site.

  DOI：

  10.1021/jm00152a014

文献信息

• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：GILEAD SCIENCES INC

  公开号：WO2010132601A1

  公开（公告）日：2010-11-18

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  这项发明涉及抗病毒化合物，含有这种化合物的组合物，包括给予这种化合物的治疗方法，以及用于制备这种化合物的过程和中间体。
• Synthesis and Anthelmintic Evaluation of Novel Valerolactam- Benzimidazole Hybrids
  作者：Beatriz Munguía、Pablo Mendina、Romina Espinosa、Andrea Lanz、Jenny Saldaña、María J. Andina、Ximena Ures、Andrés López、Eduardo Manta、Laura Domínguez

  DOI：10.2174/15701808113109990028

  日期：2013.10.1

  Some novel valerolactam derivatives of 5(6)-substituted-(1H-benzimidazol-2-yl-amine) were constructed based on the union of two structural domains with anthelmintic activity. The tested hybrid compounds 7-9 exhibited greater activity using the Nippostrongylus brasiliensis physiology-based in vitro bioassay in comparison to commercial anthelmintic benzimidazoles. Moreover, the improved physicochemical properties of hybrid compounds compared with valerolactam domain allowed the penetration of parasite barriers, concurrently with an increased intraparasitary bioavailability.

  基于具有驱虫活性的两个结构域的结合，构建了一些新颖的5(6)-取代-(1H-苯并咪唑-2-氨基)戊内酰胺衍生物。与市售的苯并咪唑类驱虫药相比，通过采用基于巴西钩口线虫生理学的体外生物测定试验，测试的杂化化合物7-9表现出更高的活性。此外，与戊内酰胺结构域相比，杂化化合物改善的物理化学性质使得它们能穿透寄生虫屏障，同时增加了寄生虫体内的生物利用度。
• Cyclic hexapeptide
  申请人：Merck & Co., Inc.

  公开号：US04192875A1

  公开（公告）日：1980-03-11

  Synthetic novel cyclic hexapeptide having the structure: ##STR1## and the dipeptide ##STR2## are prepared. Oral administration of these peptides improves the digestive efficiency of certain herbivorous animals.

  合成具有以下结构的新型循环六肽：##STR1## 以及二肽##STR2##。口服这些肽可以提高某些草食动物的消化效率。
• ANTIVIRAL COMPOUNDS
  申请人：Guo Hongyan

  公开号：US20120157404A1

  公开（公告）日：2012-06-21

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  该发明涉及抗病毒化合物、含有这些化合物的组合物以及包括给予这些化合物的治疗方法，还涉及用于制备这些化合物的过程和中间体。
• Tetrapeptide analogs
  申请人：Chao Bin

  公开号：US20100190688A1

  公开（公告）日：2010-07-29

  Compounds, compositions and methods for treatment of hyperproliferative diseases, such as cancer are provided.

  提供了用于治疗过度增殖性疾病，如癌症的化合物、组合物和方法。