1-(1,1-dimethylethyl) 2-(diphenylmethyl) (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate | 189163-46-0

• 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: 1-(1,1-dimethylethyl) 2-(diphenylmethyl) (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
• 英文别名: 2-O-benzhydryl 1-O-tert-butyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 189163-46-0
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: AZBYBUOTXNMXJV-RTBURBONSA-N

物化性质

• 沸点：
  520.3±50.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(1,1-dimethylethyl) 2-(diphenylmethyl) (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 在 18-冠醚-6 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Dipeptides bearing nucleobases for the synthesis of novel peptide nucleic acids

  摘要：

  已经制备了N-Fmoc-甘氨酰-4-(胸腺嘧啶-1-基)脯氨酸的三种立体异构体（顺式-L、反式-D和顺式-D）及其五氟苯酯，用于合成新型肽核酸。此外，还合成了N-Fmoc-甘氨酰-4-(N6-苯甲酰腺嘌呤-9-基)脯氨酸、N-Fmoc-甘氨酰-4-(N4-苯甲酰胞嘧啶-1-基)脯氨酸和N-Fmoc-甘氨酰-4-(N2-异丁酰鸟嘌呤-9-基)脯氨酸及其顺式-D系列五氟苯酯。

  DOI：

  10.1039/a603699f
• 作为产物：
  描述：

  N-Boc-顺式-4-羟基-D-脯氨酸 、 二苯基重氮甲烷 以 乙酸乙酯 为溶剂， 以90%的产率得到1-(1,1-dimethylethyl) 2-(diphenylmethyl) (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
  参考文献：
  名称：

  Dipeptides bearing nucleobases for the synthesis of novel peptide nucleic acids

  摘要：

  已经制备了N-Fmoc-甘氨酰-4-(胸腺嘧啶-1-基)脯氨酸的三种立体异构体（顺式-L、反式-D和顺式-D）及其五氟苯酯，用于合成新型肽核酸。此外，还合成了N-Fmoc-甘氨酰-4-(N6-苯甲酰腺嘌呤-9-基)脯氨酸、N-Fmoc-甘氨酰-4-(N4-苯甲酰胞嘧啶-1-基)脯氨酸和N-Fmoc-甘氨酰-4-(N2-异丁酰鸟嘌呤-9-基)脯氨酸及其顺式-D系列五氟苯酯。

  DOI：

  10.1039/a603699f

文献信息

• Chiral peptide nucleic acids
  申请人：Isis Innovation Limited

  公开号：US20020072586A1

  公开（公告）日：2002-06-13

  Chiral peptide nucleic acids are provided which hybridise strongly with complementary nucleic acids and have potential as antigene and antisense agents and as tools in molecular biology. Compounds with cis-stereochemistry and based on proline and a spacer amino acid have structures (II), (III), where n is 1 or 2-200, B is a protected or unprotected base, R is H or alkyl, aralkyl or heteroaryl and may be substituted, X may be OH, and Y may be H.

  提供了手性肽核酸，它们与互补核酸强烈杂交，并具有作为抗原和反义剂的潜力，以及作为分子生物学工具。基于脯氨酸和一个空间氨基酸的具有顺式构型的化合物具有结构（II），（III），其中n为1或2-200，B为受保护或未受保护的碱基，R为H或烷基，芳基烷基或杂环芳基，可以被取代，X可以是OH，Y可以是H。
• DNA-, RNA- and self-pairing properties of a pyrrolidinyl peptide nucleic acid with a (2′R,4′S)-prolyl-(1S,2S)-2-aminocyclopentanecarboxylic acid backbone
  作者：Jaru Taechalertpaisarn、Pitchanun Sriwarom、Chalotorn Boonlua、Nattawut Yotapan、Chotima Vilaivan、Tirayut Vilaivan

  DOI：10.1016/j.tetlet.2010.08.102

  日期：2010.11

  A new pyrrolidinyl peptide nucleic acid (PNA) comprising of an alternate sequence of 4'-nucleobase-modified proline with (2'R,4'S) configuration and a (1S,2S)-2-aminocyclopentanecarboxylic acid [(2'R,4'S)-acpcPNA] backbone was synthesized and its DNA-, RNA- and self-pairing properties studied. T-m and CD studies suggested that the (2'R,4'S)-acpcPNA forms antiparallel hybrids to DNA and RNA with high sequence and direction specificity. The stability of these hybrids is comparable to those of the (2'R,4'R)-acpcPNA hybrids previously reported by our group. On the other hand, experiments with a self-complementary sequence indicated that the new (2'R,4'S)-acpcPNA forms a more stable antiparallel self-hybrid than (2'R,4'R)-acpcPNA. (C) 2010 Elsevier Ltd. All rights reserved.
• Encoded Library Technology as a Source of Hits for the Discovery and Lead Optimization of a Potent and Selective Class of Bactericidal Direct Inhibitors of <i>Mycobacterium tuberculosis</i> InhA
  作者：Lourdes Encinas、Heather O’Keefe、Margarete Neu、Modesto J. Remuiñán、Amish M. Patel、Ana Guardia、Christopher P. Davie、Natalia Pérez-Macías、Hongfang Yang、Maire A. Convery、Jeff A. Messer、Esther Pérez-Herrán、Paolo A. Centrella、Daniel Álvarez-Gómez、Matthew A. Clark、Sophie Huss、Gary K. O’Donovan、Fátima Ortega-Muro、William McDowell、Pablo Castañeda、Christopher C. Arico-Muendel、Stane Pajk、Joaquín Rullás、Iñigo Angulo-Barturen、Emilio Álvarez-Ruíz、Alfonso Mendoza-Losana、Lluís Ballell Pages、Julia Castro-Pichel、Ghotas Evindar

  DOI：10.1021/jm401326j

  日期：2014.2.27

  Tuberculosis (TB) is one of the world's oldest and deadliest diseases, killing a person every 20 s. InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis, is the target of the frontline antitubercular drug isoniazid (INH). Compounds that directly target InhA and do not require activation by mycobacterial catalase peroxidase KatG are promising candidates for treating infections caused by INH resistant strains. The application of the encoded library technology (ELT) to the discovery of direct InhA inhibitors yielded compound 7 endowed with good enzymatic potency but with low antitubercular potency. This work reports the hit identification, the selected strategy for potency optimization, the structure-activity relationships of a hundred analogues synthesized, and the results of the in vivo efficacy studies performed with the lead compound 65.
• CHIRAL PEPTIDE NUCLEIC ACIDS
  申请人：ISIS INNOVATION LIMITED

  公开号：EP0956297A1

  公开（公告）日：1999-11-17
• [EN] CHIRAL PEPTIDE NUCLEIC ACIDS<br/>[FR] ACIDES NUCLEIQUES CHIRAUX DE PEPTIDE
  申请人：ISIS INNOVATION LIMITED

  公开号：WO1998016550A1

  公开（公告）日：1998-04-23

  (EN) Chiral peptide nucleic acids are provided which hybridise strongly with complementary nucleic acids and have potential as antigene and antisense agents and as tools in molecular biology. Compounds with cis-stereochemistry and based on proline and a spacer amino acid have structures (II), (III), where n is 1 or 2 - 200, B is a protected or unprotected base, R is H or alkyl, aralkyl or heteroaryl and may be substituted, X may be OH, and Y may be H.(FR) L'invention concerne des acides nucléiques chiraux de peptides qui s'hybrident solidement à des acides nucléiques complémentaires, sont des agents antigéniques et anti-sens potentiels, et peuvent être utilisés en biologie moléculaire. Des composés avec cis-stéréochimie et basés sur de la proline et sur un espaceur acide aminé sont de structure (II), (III), où n est égal à 1 ou va de 2 à 200, B est une base protégée ou exposée, R est H ou alkyle, aralkyle ou hétéroalkyle et peut être substitué, X peut être OH, et Y peut être H.