benzhydrylidene aza-glycinyl-proline | 1108148-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzhydrylidene aza-glycinyl-proline
• 英文别名: benzophenone aza-Gly-Pro-OH；(2S)-1-[(benzhydrylideneamino)carbamoyl]pyrrolidine-2-carboxylic acid
• CAS: 1108148-69-1
• 化学式: C₁₉H₁₉N₃O₃
• 分子量: 337.378
• InChiKey: ZEUAVIJWPPKMDD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzhydrylidene aza-glycinyl-proline 在 盐酸 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Azopeptides: Synthesis and Pericyclic Chemistry

  摘要：

  Azopeptides possess an imino urea as an amino amide surrogate in the sequence. Azopeptides were synthesized by oxidation of aza-glycine residues and employed in pericyclic chemistry. Diels-Alder cyclizations and Alder-ene reactions on azopeptides enabled construction of constrained aza-pipecolyl and reactive aza-allylglycyl residues. X-ray crystallographic analyses of azopeptide 16a and azapeptides 30a and 35a provided insight into imino urea configuration and conformational affects of cycloalkane side chains at the semicarbazide alpha- and beta-nitrogen, respectively.

  DOI：

  10.1021/acs.orglett.5b02723
• 作为产物：
  描述：

  二苯甲酮腙 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 benzhydrylidene aza-glycinyl-proline
  参考文献：
  名称：

  氮杂二肽结构单元的溶液相亚单体多样化及其在氮杂肽和氮杂DKP合成中的应用。

  摘要：

  在针对药物发现和化学生物学的计划中，氮杂肽已用作研究SAR的工具。受保护的氮杂二肽是通过溶液相亚单体方法合成的，该方法以叔丁醇钾为碱，使用不同的烷基卤化物对N末端二苯甲酮半脲酮氮杂Gly-Xaa二肽进行烷基化。苯甲酮保护的氮杂二肽叔丁酯31c在C端酯或N处选择性脱保护末端分别提供氮杂二肽酸和胺结构单元36c和40c，它们被引入到更长的氮杂肽中。另外，从氮杂-二肽甲酯29a-c中去除二苯甲酮半脲酮保护导致分子内环化生成aza-DKPs 39a-c。鉴于氮杂肽和DKP作为治疗剂和生物过程探针的重要性，这种面向多样性的解决方案阶段方法可能为研究肽科学提供有用的工具。版权所有©2010欧洲肽协会和John Wiley＆Sons，Ltd.。

  DOI：

  10.1002/psc.1235

文献信息

• PROSTAGLANDIN-F2 ALPHA RECEPTOR MODULATORS AND USES THEREOF
  申请人：LUBELL William D.

  公开号：US20120309690A1

  公开（公告）日：2012-12-06

  Prostaglandin-F2 alpha (PGF2α) receptor (FP) modulators of formula I, as well as the use of PGF2α receptor modulators for the treatment of conditions associated with FP activity such as preterm labor and colorectal cancer, are disclosed.

  本文揭示了公式I的前列腺素F2α（PGF2α）受体（FP）调节剂，以及使用PGF2α受体调节剂治疗与FP活性相关的疾病，例如早产和结直肠癌的方法。
• Targeting the Prostaglandin F2α Receptor for Preventing Preterm Labor with Azapeptide Tocolytics
  作者：Carine B. Bourguet、Eugénie Goupil、Danaë Tassy、Xin Hou、Eryk Thouin、Felix Polyak、Terence E. Hébert、Audrey Claing、Stéphane A. Laporte、Sylvain Chemtob、William D. Lubell

  DOI：10.1021/jm200608k

  日期：2011.9.8

  The prostaglandin-F2 alpha (PGF2 alpha) receptor (FP) was targeted to develop tocolytic agents for inhibiting preterm labor. Azabicycloalkane and azapeptide mimics 2-10 were synthesized based on the (3S,6S,9S)-indolizidin-2-one amino acid analogue PDC113.824 (1), which was shown to modulate FP by a biased allosteric mechanism, involving both G alpha q- and G alpha 12-mediated signaling pathways, and exhibited significant tocolytic activity delaying preterm labor in a mouse model (Goupil; J. Biol. Chem. 2010, 285,25624-25636), Although changes in azabicycloalkane stereochemistry and ring size caused loss of activity, replacement of the indolizidin-2-one amino acid with azaGly-Pro and azaPhe-Pro gave azapeptides 6 and 8, which reduced PGF2 alpha-induced myometrial contractions, potentiated the effect of PGF2 alpha on G alpha q-mediated ERK1/2 activation, and inhibited FP modulation of cell ruffling, a response dependent on the G alpha 12/RhoA/ROCK signaling pathway. Revealing complementarities of azabicycloalkane and azapeptide mimics, novel probes, and efficient tocolytic agents were made to study allosteric modulation of the FP receptor.
• PEPTIDOMIMETIC AGENTS, SYNTHESIS AND USES THEREOF
  申请人：THE FEINSTEIN INSTITUTES FOR MEDICAL RESEARCH

  公开号：US20200354404A1

  公开（公告）日：2020-11-12

  Compounds for use in synthesis of peptidomimetic agents; synthesis of peptidomimetic agents; peptidomimetic diagnostic and therapeutic agents; and uses of the compounds and peptidomimetic agents in drug discovery, diagnosis, prevention and treatment of diseases are described.
• US8802818B2
  申请人：——

  公开号：US8802818B2

  公开（公告）日：2014-08-12
• Solution-phase submonomer diversification of aza-dipeptide building blocks and their application in aza-peptide and aza-DKP synthesis
  作者：Carine B. Bourguet、Caroline Proulx、Sophie Klocek、David Sabatino、William D. Lubell

  DOI：10.1002/psc.1235

  日期：2010.6

  Aza‐peptides have been used as tools for studying SARs in programs aimed at drug discovery and chemical biology. Protected aza‐dipeptides were synthesized by a solution‐phase submonomer approach featuring alkylation of N‐terminal benzophenone semicarbazone aza‐Gly‐Xaa dipeptides using different alkyl halides in the presence of potassium tert‐butoxide as base. Benzophenone protected aza‐dipeptide tert‐butyl

  在针对药物发现和化学生物学的计划中，氮杂肽已用作研究SAR的工具。受保护的氮杂二肽是通过溶液相亚单体方法合成的，该方法以叔丁醇钾为碱，使用不同的烷基卤化物对N末端二苯甲酮半脲酮氮杂Gly-Xaa二肽进行烷基化。苯甲酮保护的氮杂二肽叔丁酯31c在C端酯或N处选择性脱保护末端分别提供氮杂二肽酸和胺结构单元36c和40c，它们被引入到更长的氮杂肽中。另外，从氮杂-二肽甲酯29a-c中去除二苯甲酮半脲酮保护导致分子内环化生成aza-DKPs 39a-c。鉴于氮杂肽和DKP作为治疗剂和生物过程探针的重要性，这种面向多样性的解决方案阶段方法可能为研究肽科学提供有用的工具。版权所有©2010欧洲肽协会和John Wiley＆Sons，Ltd.。