benzyl tert-butyl (3-(methoxy(methyl)amino)-3-oxopropane-1,2-diyl)(S)-dicarbamate | 186603-76-9

• 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: benzyl tert-butyl (3-(methoxy(methyl)amino)-3-oxopropane-1,2-diyl)(S)-dicarbamate
• CAS: 186603-76-9
• 化学式: C₁₈H₂₇N₃O₆
• 分子量: 381.429
• InChiKey: LYRDBDBGPVBJMU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106.2
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl tert-butyl (3-(methoxy(methyl)amino)-3-oxopropane-1,2-diyl)(S)-dicarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Capped diaminopropionamide–glycine dipeptides are inhibitors of CC chemokine receptor 2 (CCR2)

  摘要：

  A new series of CCR2 antagonists has been discovered that incorporates intramolecular hydrogen bonding as a strategy for rigidifying the scaffold. The structure-activity relationship was established through initial systematic modification of substitution pattern and chain length, followed by independent optimization of three different substituents (benzylamine, carboxamide, and benzamide). Several of the acyclic compounds display 10-30 nM binding affinity for CCR2. Moreover, these antagonists are able to block both MCP-1-induced Ca2+ flux and monocyte chemotaxis, and are selective for binding to CCR2 over CCR1 and CCR3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.028
• 作为产物：
  描述：

  N-叔丁氧羰基-3-[(苄氧羰基)氨基]-L-丙氨酸 、 N-甲基-N-甲氧基胺盐酸盐 在 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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl tert-butyl (3-(methoxy(methyl)amino)-3-oxopropane-1,2-diyl)(S)-dicarbamate
  参考文献：
  名称：

  Capped diaminopropionamide–glycine dipeptides are inhibitors of CC chemokine receptor 2 (CCR2)

  摘要：

  A new series of CCR2 antagonists has been discovered that incorporates intramolecular hydrogen bonding as a strategy for rigidifying the scaffold. The structure-activity relationship was established through initial systematic modification of substitution pattern and chain length, followed by independent optimization of three different substituents (benzylamine, carboxamide, and benzamide). Several of the acyclic compounds display 10-30 nM binding affinity for CCR2. Moreover, these antagonists are able to block both MCP-1-induced Ca2+ flux and monocyte chemotaxis, and are selective for binding to CCR2 over CCR1 and CCR3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.028

文献信息

• Synthesis of Tetrasubstituted Symmetrical Pyrazines from β-Keto γ-Amino Esters: A Mild Strategy for Self-Dimerization of Peptides
  作者：Mothukuri Ganesh Kumar、Varsha J. Thombare、Rupal D. Bhaisare、Anindita Adak、Hosahudya N. Gopi

  DOI：10.1002/ejoc.201403237

  日期：2015.1

  facile synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial oxidation of β-keto γ-amino esters is reported. The scope of the reaction was examined by use of various amino acid side-chain functional groups and peptides. The mild and efficient transformation of β-keto γ-amino esters into pyrazines may serve as an attractive strategy for self-dimerization of peptides.

  报道了通过 β-酮基 γ-氨基酯的简单空气氧化轻松合成高度对称的四取代吡嗪。通过使用各种氨基酸侧链官能团和肽来检查反应范围。β-酮基γ-氨基酯温和有效地转化为吡嗪类化合物可以作为一种有吸引力的肽自二聚化策略。
• Discovery of an orally-bioavailable CC Chemokine Receptor 2 antagonist derived from an acyclic diaminoalcohol backbone
  作者：Percy H. Carter、Gregory D. Brown、Sarah R. King、Matthew E. Voss、Andrew J. Tebben、Robert J. Cherney、Sandhya Mandlekar、Yvonne C. Lo、Gengjie Yang、Persymphonie B. Miller、Peggy A. Scherle、Qihong Zhao、Carl P. Decicco

  DOI：10.1016/j.bmcl.2012.03.007

  日期：2012.5

  We describe an isostere-driven approach to improve upon a previously-described series of capped dipeptide antagonists of CC Chemokine Receptor 2 (CCR2). Modification of the substitution around the isostere was combined with additional changes in a distal aromatic substituent to provide single-digit nanomolar antagonists of CCR2. These studies led to the identification of 18, a compound that was suitable for studies in murine models of CCR2 activity. (C) 2012 Elsevier Ltd. All rights reserved.