fmoc-aza-β3-ala | 512856-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: fmoc-aza-β3-ala
• 英文别名: Fmoc-aza-β3-Ala-OH；FmocNHNMe(CH2COOH)；(N-Fmoc-N'-methyl hydrazino)-acetic acid；2-[(9H-fluoren-9-ylmethoxycarbonylamino)-methylamino]acetic acid
• CAS: 512856-46-1
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: YMNGQVVITHIUGI-UHFFFAOYSA-N

物化性质

• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟乙酸五氟苯酯 、 fmoc-aza-β3-ala 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [N'-(9H-Fluoren-9-ylmethoxycarbonyl)-N-methyl-hydrazino]-acetic acid pentafluorophenyl ester
  参考文献：
  名称：

  带有N-氨基-N-甲基甘氨酸间隔基的新型吡咯烷基PNA的合成及核酸结合研究

  摘要：

  使用固相方法合成了两个新的吡咯烷基肽核酸，它们包含胸腺嘧啶修饰的d-或l-脯氨酸和N-氨基-N-甲基甘氨酸间隔区的交替序列。UV和CD滴定以及凝胶结合移位试验表明，高氨苄胸腺嘧啶PNA十聚体均不与它们的互补DNA或RNA结合。认为这是由于不利的二级结构所致，而该二级结构不能被PNA主链中带正电荷的质子化胺所缓解。

  DOI：

  10.1016/s0040-4039(03)00033-9
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 以100%的产率得到fmoc-aza-β3-ala
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7

文献信息

• 一种Fmoc-Aza-β³-Ala的合成方法
  申请人：杭州瑞岚得医疗科技有限公司

  公开号：CN108178740A

  公开（公告）日：2018-06-19

  本发明公开了一种Fmoc‑Aza‑β 3 ‑Ala的合成方法，所述的方法为：用过量的二碳酸二叔丁酯处理甲基肼得到式B1所示的化合物1，向所得式B1所示的化合物1中加入Fmoc‑cl和NaHCO 3 发生亲核取代得到式B2所示的化合物2，用三氟乙酸(TFA)或HCLG酸化所得式B2所示的化合物2，使Boc保护基团断裂得到式B3所示的化合物3；将所得式B3所示的化合物3与溴乙酸叔丁酯发生亲核取代得到式A4所示的化合物4；将所得式A4所示的化合物4与通有HCl气体的二氯甲烷进行脱脂反应得到式B5所示的目标产物Fmoc‑Aza‑β 3 ‑Ala。本发明所述的制备方法，反应条件温和，Fmoc保护基团可以很容易地使用温和碱性条件除去，操作简便，酸不稳定基团可用于保护侧链，路线简单高效。
• Peptide analogues comprising at least one type of aminoacylaza-$g(b)<sp>3</sp>and the use thereof, in particular for therapy
  申请人：Baudy Floc'h Michele

  公开号：US20110044974A1

  公开（公告）日：2011-02-24

  The object of the present invention is analogues of peptides or parent proteins, these peptide analogues, comprising at least one aza-β 3 aminoacyl residue, and also their uses in pharmaceutical compositions or for the diagnosis of pathologies wherein the aforesaid peptides or parent proteins are involved.

  本发明的对象是肽或母体蛋白的类似物，这些肽类似物包括至少一个aza-β3氨基酰残基，并且它们在药物组合物中的用途或用于诊断涉及上述肽或母体蛋白的病理的用途。
• REVERSE-TURN MIMETICS AND METHOD RELATING THERETO
  申请人：Moon Sung Hwan

  公开号：US20100029630A1

  公开（公告）日：2010-02-04

  Conformationally constrained compounds that mimic the secondary structure of reverse-turn regions of biologically active peptides and proteins are disclosed. Such reverse-turn mimetic structures have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the reverse-turn mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members. The invention also relates to the use of such compounds for inhibiting or treating disorders modulated by Wnt-signaling pathway, such as cancer, especially colorectal cancer, restenosis associated with angioplasty, polycystic kidney disease, aberrant angiogenesis disease, rheumatoid arthritis disease, tuberous sclerosis complex, Alzheimer's disease, excess hair growth or loss, or ulcerative colitis.

  本文揭示了具有构象约束的化合物，其模拟生物活性肽和蛋白质的反转区域的二级结构。这种反转区域模拟结构在广泛的领域中具有实用性，包括用作诊断和治疗剂。本发明还揭示了包含这种反转区域模拟结构的文库，以及筛选这些文库以识别具有生物活性成员的方法。本发明还涉及使用这些化合物来抑制或治疗由Wnt信号通路调节的疾病，例如癌症，特别是结肠直肠癌，与血管成形术相关的再狭窄，多囊肾病，异常血管生成疾病，类风湿性关节炎疾病，结节性硬化症，阿尔茨海默病，过度生长或脱发，或溃疡性结肠炎。
• Reverse-turn mimetics and method relating thereto
  申请人：Moon Hwan Sung

  公开号：US20070021425A1

  公开（公告）日：2007-01-25

  Conformationally constrained compounds that mimic the secondary structure of reverse-turn regions of biologically active peptides and proteins are disclosed. Such reverse-turn mimetic structures have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the reverse-turn mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members. The invention also relates to the use of such compounds for inhibiting or treating disorders modulated by Wnt-signaling pathway, such as cancer, especially colorectal cancer, restenosis associated with angioplasty, polycystic kidney disease, aberrant angiogenesis disease, rheumatoid arthritis disease, tuberous sclerosis complex, Alzheimer's disease, excess hair growth or loss, or ulcerative colitis.

  本发明揭示了能够模拟生物活性肽和蛋白质的反转区域的二级结构的构象限制化合物。这种反转区域拟态结构在广泛的领域中具有实用性，包括用作诊断和治疗剂。本发明还揭示了包含这种反转区域拟态结构的库，以及筛选这些库以识别生物活性成员的方法。本发明还涉及使用这些化合物来抑制或治疗由Wnt信号通路调节的疾病，例如癌症，特别是结直肠癌，与血管成形术相关的再狭窄，多囊肾病，异常血管生成疾病，类风湿性关节炎疾病，结节性硬化症，阿尔茨海默病，过度生发或脱发，或溃疡性结肠炎。
• [EN] REVERSE-TURN MIMETICS AND METHOD RELATING THERETO<br/>[FR] MIMETIQUES A ROTATION INVERSE ET PROCEDE ASSOCIE
  申请人：CHOONGWAE PHARMA CORP

  公开号：WO2005116032A3

  公开（公告）日：2006-04-13