tert-butyl [(2S)-1-(methylamino)-1-oxo-3-(pyridin-4-yl)propan-2-yl]carbamate | 139178-65-7

• 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 [(2S)-1-(methylamino)-1-oxo-3-(pyridin-4-yl)propan-2-yl]carbamate
• 英文别名: tert-butyl N-[(2S)-1-(methylamino)-1-oxo-3-pyridin-4-ylpropan-2-yl]carbamate
• CAS: 139178-65-7
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: IEDSOSAKCMQDFB-NSHDSACASA-N

物化性质

• 沸点：
  511.8±50.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl [(2S)-1-(methylamino)-1-oxo-3-(pyridin-4-yl)propan-2-yl]carbamate 在 platinum(IV) oxide 、 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 50.0h， 生成 (2S)-N-[(2S)-3-[1-(3-tert-butyl-1-methyl-1H-pyrazole-5-carbonyl)piperidin-4-yl]-1-(methylamino)-1-oxopropan-2-yl]-6-oxopiperidine-2-carboxamide
  参考文献：
  名称：

  Characterization of Specific N-α-Acetyltransferase 50 (Naa50) Inhibitors Identified Using a DNA Encoded Library

  摘要：

  Two novel compounds were identified as Naa50 binders/inhibitors using DNA-encoded technology screening. Biophysical and biochemical data as well as cocrystal structures were obtained for both compounds (3a and 4a) to understand their mechanism of action. These data were also used to rationalize the binding affinity differences observed between the two compounds and a MLGP peptide-containing substrate. Cellular target engagement experiments further confirm the Naa50 binding of 4a and demonstrate its selectivity toward related enzymes (Naa10 and Naa60). Additional analogs of inhibitor 4a were also evaluated to study the binding mode observed in the cocrystal structures.

  DOI：

  10.1021/acsmedchemlett.0c00029
• 作为产物：
  描述：

  Boc-3-(4-吡啶基)-L-丙氨酸 、 甲胺 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl [(2S)-1-(methylamino)-1-oxo-3-(pyridin-4-yl)propan-2-yl]carbamate
  参考文献：
  名称：

  肽折叠夹的金属驱动组装：分子带的形成†

  摘要：

  在本文中，我们报告了肽折叠蛋白在超分子金属有机结构合成中的应用。通过X射线衍射分析证实，设计并合成了肽配体，以采用在两端均带有吡啶基配体的规范3 10螺旋。在适当的反应条件下合成的肽和银盐的结合导致配位聚合物的产生。由此产生的材料已经通过SEM-EDS进行了分析，证实了长的，规则的，带状纤维的形成，该纤维同时包含有机部分和金属原子。ATR FT-IR光谱表明该肽的螺旋结构保留在纤维内。

  DOI：

  10.1039/c6ce00601a

文献信息

• Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study
  作者：Daniel E. Levy、France Lapierre、Weisheng Liang、Wenqing Ye、Christopher W. Lange、Xiaoyuan Li、Damian Grobelny、Marie Casabonne、David Tyrrell、Kevin Holme、Alex Nadzan、Richard E. Galardy

  DOI：10.1021/jm970494j

  日期：1998.1.1

  Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess strong zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.
• PHOSPHONOPEPTIDES WITH COLLAGENASE INHIBITING ACTIVITY
  申请人：Beecham Group p.l.c.

  公开号：EP0527764A1

  公开（公告）日：1993-02-24
• US5994312A
  申请人：——

  公开号：US5994312A

  公开（公告）日：1999-11-30
• US6180611B1
  申请人：——

  公开号：US6180611B1

  公开（公告）日：2001-01-30
• [EN] PHOSPHONOPEPTIDES WITH COLLAGENASE INHIBITING ACTIVITY
  申请人：BEECHAM GROUP PLC

  公开号：WO1991015507A1

  公开（公告）日：1991-10-17

  (EN) Phosphorous derivatives having structure (I), processes for their preparation and their use as collagenase inhibitors.(FR) Dérivés phosphoreux correspondant à la structure (I), procédés de préparation et utilisation comme inhibiteurs de collagénase.