3H-吡咯-3-酮,1,2-二氢-4,5-二甲基-2-(1-甲基亚乙基)- | 218926-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 3H-吡咯-3-酮,1,2-二氢-4,5-二甲基-2-(1-甲基亚乙基)-
• 中文别名: N-[(9H-芴-9-基甲氧基)羰基]-2-丙基正缬氨酸；Fmoc-双丙基甘氨酸；FMOC-二丁基甘氨酸
• 英文名称: N-(9-fluorenylmethyloxycarbonyl)-α,α-dipropylglycine
• 英文别名: Fmoc-Dpg-OH；Fmoc-Dipropylglycine；2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-propylpentanoic acid
• CAS: 218926-47-7
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: FIHDROCXVRQYAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3H-吡咯-3-酮,1,2-二氢-4,5-二甲基-2-(1-甲基亚乙基)- 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Sureshbabu, Vommina V.; Chennakrishnareddy, Gundala, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 7, p. 981 - 988

  摘要：

  DOI：
• 作为产物：
  描述：

  二-n-丙基甘氨酸 、 氯甲酸-9-芴基甲酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 以87%的产率得到3H-吡咯-3-酮,1,2-二氢-4,5-二甲基-2-(1-甲基亚乙基)-
  参考文献：
  名称：

  Synthesis and biological activity of nociceptin/orphanin FQ analogues substituted in position 7 or 11 with Cα,α-dialkylated amino acids

  摘要：

  Previous structure-activity and NMR studies on nociceptin/orphanin FQ (N/OFQ) demonstrated that Aib substitution of Ala(7) and/or Ala(11) increases the peptide potency through an alpha helix structure induction mechanism. On these bases we synthesised and evaluated pharmacologically in the mouse vas deferens assay a series of N/OFQ-NH2 analogues substituted in position 7 and 11 with C alpha,alpha-disubstituted cyclic, linear and branched amino acids. None of the 20 novel N/OFQ analogues produced better results than [Aib(7)]N/OFQ-NH2. Thus, this substitution was combined with other chemical modifications known to modulate peptide potency and/or efficacy generating compound 21 [Nphe(1)Aib(7) Arg(14) Lys(15)] N/OFQ-NH2 (coded as UFP- 111), compound 22 [(pF)Phe(4) Aib(7) Arg(14) Lys(15)] N/OFQ-NH2 (UFP-112) and compound 23 [Phe psi(CH2-NH)Gly(2) (pF)Phe(4)Aib(7)Arg(14)Lys(15)]N/OFQ-NH2 (UFP- 113). These novel peptides behaved as highly potent NOP receptor ligands showing full (UFP- 112) and partial (UFP- 113) agonist and pure antagonist (UFP- 111) activities in a series of in vitro functional assays performed on pharmacological preparations expressing native as well as recombinant NOP receptors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.026

文献信息

• Babu, Vommina V. Suresh; Ananda, Kuppanna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 1, p. 70 - 74
  作者：Babu, Vommina V. Suresh、Ananda, Kuppanna

  DOI：——

  日期：——
• Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of type 2 diabetes: 1. Identification of 1-amino-1-cycloalkyl carboxylic acid headgroups
  作者：Steven M. Sparks、Pierette Banker、David M. Bickett、H. Luke Carter、Daphne C. Clancy、Scott H. Dickerson、Kate A. Dwornik、Dulce M. Garrido、Pamela L. Golden、Robert T. Nolte、Andrew J. Peat、Lauren R. Sheckler、Francis X. Tavares、Stephen A. Thomson、Liping Wang、James E. Weiel

  DOI：10.1016/j.bmcl.2008.11.085

  日期：2009.2

  Optimization of the amino acid residue within a series of anthranilimide-based glycogen phosphorylase inhibitors is described. These studies culminated in the identification of anthranilimides 16 and 22 which displayed potent in vitro inhibition of GPa in addition to reduced inhibition of CYP2C9 and excellent pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.
• Peptaibolin analogues by incorporation of α,α-dialkylglycines: synthesis and study of their membrane permeating ability
  作者：Vânia I.B. Castro、Carina M. Carvalho、Rui D.V. Fernandes、Sílvia M.M.A. Pereira-Lima、Elisabete M.S. Castanheira、Susana P.G. Costa

  DOI：10.1016/j.tet.2015.12.079

  日期：2016.2

  Analogues of Peptaibolin, a peptaibol with antibiotic activity, incorporating alpha,alpha-dialkylglycines (Deg, Dpg, and Ac(6)c) at selected positions were synthesised by MW-SPPS and fully characterized. A control analogue incorporating L-alanine was also prepared. The native peptide and the analogues were studied by fluorescence spectroscopy for their membrane permeating activity. Small unilamellar vesicles (SUVs) of egg phosphatidylcholine/cholesterol (70:30) containing an encapsulated fluorescence probe (6-carboxyfluorescein) were used as membrane models. The assays of carboxyfluorescein release from SUVs upon peptide addition showed that Peptaibolin-Dpg and Peptaibolin-Ac(6)c are the most active peptides. These results indicate that the structure of the alpha,alpha-diallcylglycines is crucial for the membrane permeating ability of these Peptaibolin analogues. (C) 2016 Elsevier Ltd. All rights reserved.
• Thermodynamic and Structural Impact of α,α-Dialkylated Residue Incorporation in a β-Hairpin Peptide
  作者：Megan A. Karnes、Shelby L. Schettler、Halina M. Werner、Alana F. Kurz、W. Seth Horne、George A. Lengyel

  DOI：10.1021/acs.orglett.6b01936

  日期：2016.8.5

  Peptides containing alpha,alpha-dialkylated alpha-amino acids, owing to their ability to disrupt aggregation of beta-amyloid proteins, have therapeutic potential in the treatment of neurodegenerative diseases. Thermodynamic and structural analyses are reported for a series of beta-hairpin peptides containing alpha,alpha-dialkylated alpha-amino acids with varying side chain lengths. The results of these experiments show that alpha,alpha-dialkylated alpha-amino acids with side-chain lengths longer than one carbon unit are tolerated in a beta-hairpin, although at a moderate cost to folded stability.
• Facile Synthesis of α,α-Diisobutylglycine and Anchoring Its Derivatives onto PAL-PEG-PS Resin
  作者：Yanwen Fu、Marcus A. Etienne、Robert P. Hammer

  DOI：10.1021/jo034885j

  日期：2003.12.1

  alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N-alpha-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are used for anchoring alphaalphaAAs onto a trialkoxybenzyl linker on PEG-PS grafted support, upon which a beta-strand mimic with difficult sequence is assembled in a superior quality.