(4R)-benzyl 2,2-dioxo-3-(9-fluorenylmethoxycarbonyl)-1,2,3-oxathiazinane-4-carboxylate | 1160862-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4R)-benzyl 2,2-dioxo-3-(9-fluorenylmethoxycarbonyl)-1,2,3-oxathiazinane-4-carboxylate
• 英文别名: (4R)-benzyl-2,2-dioxo-3-(9-fluorenylmethoxycarbonyl)-1,2,3-oxathiazinane-4-carboxylate；4-O-benzyl 3-O-(9H-fluoren-9-ylmethyl) (4R)-2,2-dioxooxathiazinane-3,4-dicarboxylate
• CAS: 1160862-48-5
• 化学式: C₂₆H₂₃NO₇S
• 分子量: 493.537
• InChiKey: ZSLUIQJQRBKNFR-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R)-benzyl 2,2-dioxo-3-(9-fluorenylmethoxycarbonyl)-1,2,3-oxathiazinane-4-carboxylate 、 在 N,O-双三甲硅基乙酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Structure–Activity Analysis of the Growth Hormone Secretagogue GHRP-6 by α- and β-Amino γ-Lactam Positional Scanning

  摘要：

  Incorporation of amino lactams into biologically active peptides restricts conformational mobility and may enhance selectivity and increase potency. α‐ and β‐amino γ‐lactams (Agl and Bgl), in both S and R configurations, were introduced into the growth hormone secretagogue GHRP‐6 using a Fmoc‐compatible solid‐phase protocol relying on N‐alkylation with five‐ and six‐membered cyclic sulfamidates, followed by lactam annulation under microwave heating. Using this protocol in conjunction with IRORI KanTM techniques furnished eleven new GHRP‐6 analogs, and their binding affinity IC50 values on both the growth hormone secretagogue receptor 1a (GHS‐R1a) and CD36 receptors are herein reported. The results indicate that selectivity towards one receptor or the other can be modulated by lactam substitution, typically at the Ala3 and the d‐Phe5 positions.

  DOI：

  10.1111/j.1747-0285.2009.00913.x
• 作为产物：
  描述：

  (2SR,4R)-benzyl 2-oxo-3-(9-fluorenylmethoxycarbonyl)-1,2,3-oxathiazinane-4-carboxylate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以92%的产率得到(4R)-benzyl 2,2-dioxo-3-(9-fluorenylmethoxycarbonyl)-1,2,3-oxathiazinane-4-carboxylate
  参考文献：
  名称：

  Jamieson, Andrew G.; Boutard, Nicolas; Beauregard, Kim, Journal of the American Chemical Society, 2009, vol. 131, p. 7917 - 7927

  摘要：

  DOI：

文献信息

• [EN] PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE GAMMA-LACTAMES AMINO-SUBSTITUÉS
  申请人：VALORISATION RECH SOC EN COMMA

  公开号：WO2010105367A1

  公开（公告）日：2010-09-23

  The present application describes general process for the preparation of amino-substitued gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substitued gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.

  本申请描述了一般的氨基取代γ-内酰胺的制备过程，涉及到通式(I)和(VI)的合成子与胺的反应。这些过程适用于固相合成技术，因此可以有效地将氨基取代γ-内酰胺并入各种结构支架中，特别是肽类结构。
• PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS
  申请人：Lubell William

  公开号：US20120101257A1

  公开（公告）日：2012-04-26

  The present application describes general process for the preparation of amino-substituted gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substituted gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.

  该申请书描述了一种制备氨基取代的γ-内酰胺的通用过程，包括将通式(I)和(VI)的合成物与胺反应。这些过程适用于固相合成技术，因此可以有效地将氨基取代的γ-内酰胺纳入各种结构支架中，特别是肽中。
• [EN] PEPTIDOMIMETICS FOR MODULATING INTERLEUKIN-1 RECEPTOR<br/>[FR] PEPTIDOMIMÉTIQUES POUR MODULER LE RÉCEPTEUR D'INTERLEUKINE-1
  申请人：CT HOSPITALIER UNIVERSITAIRE S

  公开号：WO2010106441A2

  公开（公告）日：2010-09-23

  The present invention provides, among other things, improved Allosteramers™ for modulating IL-I receptor activity. In particular, the present invention provides peptidomimetics containing lactams and/or Bab residues. Pharmaceutical compositions of the peptidomimetic compounds of the present invention and methods of using these compositions in the treatment of various disorders are also provided.
• Jamieson, Andrew G.; Boutard, Nicolas; Beauregard, Kim, Journal of the American Chemical Society, 2009, vol. 131, p. 7917 - 7927
  作者：Jamieson, Andrew G.、Boutard, Nicolas、Beauregard, Kim、Bodas, Mandar S.、Ong, Huy、et al.

  DOI：——

  日期：——
• Structure–Activity Analysis of the Growth Hormone Secretagogue GHRP-6 by α- and β-Amino γ-Lactam Positional Scanning
  作者：Nicolas Boutard、Andrew G. Jamieson、Huy Ong、William D. Lubell

  DOI：10.1111/j.1747-0285.2009.00913.x

  日期：2010.1

  Incorporation of amino lactams into biologically active peptides restricts conformational mobility and may enhance selectivity and increase potency. α‐ and β‐amino γ‐lactams (Agl and Bgl), in both S and R configurations, were introduced into the growth hormone secretagogue GHRP‐6 using a Fmoc‐compatible solid‐phase protocol relying on N‐alkylation with five‐ and six‐membered cyclic sulfamidates, followed by lactam annulation under microwave heating. Using this protocol in conjunction with IRORI KanTM techniques furnished eleven new GHRP‐6 analogs, and their binding affinity IC50 values on both the growth hormone secretagogue receptor 1a (GHS‐R1a) and CD36 receptors are herein reported. The results indicate that selectivity towards one receptor or the other can be modulated by lactam substitution, typically at the Ala3 and the d‐Phe5 positions.