N-Boc-N-butylglycine | 439287-56-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Boc-N-butylglycine
• 英文别名: 2-(N,N-tert-butoxycarbonyl-n-butylamino)acetic acid；N-Boc-N-butyl-glycine；2-[butyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid
• CAS: 439287-56-6
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: GVIPZPIGOBQFNC-UHFFFAOYSA-N

物化性质

• 沸点：
  333.9±21.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Boc-N-butylglycine 在 N-甲基吗啉 、 盐酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.08h， 生成 (+/-)-2-(n-butylamino)-N-(α-methylbenzyl)acetamide hydrochloride
  参考文献：
  名称：

  Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

  摘要：

  Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(alpha -methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl-2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the alpha -methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg(-1), TD50 = 36.4 mg kg(-1), PI = 6.3). Replacement of the piperidine ring of I by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01206-x
• 作为产物：
  描述：

  乙基N-丁基甘氨酸酯 在 sodium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 生成 N-Boc-N-butylglycine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

  摘要：

  Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(alpha -methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl-2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the alpha -methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg(-1), TD50 = 36.4 mg kg(-1), PI = 6.3). Replacement of the piperidine ring of I by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01206-x

文献信息

• [EN] PIPERIDINE SUBSTITUTED TRICYCLIC PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES WITH INHIBITORY ACTIVITY ON THE REPLICATION OF THE RESPIRATORY SYNCYTIAL VIRUS (RSV)<br/>[FR] DÉRIVÉS TRICYCLIQUES DE PYRAZOLO [1,5-A] PYRIMIDINE SUBSTITUÉS PAR PIPÉRIDINE, AYANT UNE ACTIVITÉ INHIBITRICE SUR LA RÉPLICATION DU VIRUS RESPIRATOIRE SYNCYTIAL (RSV)
  申请人：JANSSEN SCIENCES IRELAND UC

  公开号：WO2016091791A1

  公开（公告）日：2016-06-16

  The invention concerns novel substituted tricyclic pyrazolo pyrimidine compounds of formula (I-a) or (I-b) having antiviral activity, in particular, having an inhibitory activity on the replication of the respiratory syncytial virus (RSV). The invention further concerns the preparation of such novel compounds, compositions comprising these compounds, and the compounds for use in the treatment of respiratory syncytial virus infection.

  该发明涉及具有抗病毒活性的新型取代三环吡唑吡嘧啶化合物，特别是对呼吸道合胞病毒（RSV）复制具有抑制活性的化合物，其化学式为（I-a）或（I-b）。该发明还涉及制备这种新型化合物、含有这些化合物的组合物以及用于治疗呼吸道合胞病毒感染的化合物。
• Cyclic Poly(α-peptoid)s and Their Block Copolymers from N-Heterocyclic Carbene-Mediated Ring-Opening Polymerizations of N-Substituted <i>N</i>-Carboxylanhydrides
  作者：Li Guo、Donghui Zhang

  DOI：10.1021/ja907380d

  日期：2009.12.23

  sequential monomer addition. The cyclic polymer architectures were verified by MALDI-TOF mass spectrometry and intrinsic viscosity measurements. Mark-Houwink-Sakurada plot analyses revealed that cyclic poly(alpha-peptoid)s prepared from NHC-mediated polymerizations exhibit lower intrinsic viscosities than their linear analogues prepared from primary amine-initiated polymerizations. The ratio of their intrinsic

  N-取代的 N-羧基酐 ((N)R-NCA) 的 N-杂环卡宾 (NHC) 介导的开环聚合 (ROP) 产生具有受控分子量 (M(n) = 3-30 kg mol(-1)) 和窄分子量分布 (PDI = 1.04-1.12)。该反应表现出具有最小链转移的活性聚合特征。这使得可以通过顺序单体添加轻松合成环状二嵌段共聚（α-拟肽）。通过 MALDI-TOF 质谱和特性粘度测量验证了环状聚合物结构。Mark-Houwink-Sakurada 绘图分析显示，由 NHC 介导的聚合制备的环状聚 (α-拟肽) 比由伯胺引发的聚合制备的线性类似物具有更低的特性粘度。
• Chemical compounds
  申请人：Wiley Robert Michael

  公开号：US20050026928A1

  公开（公告）日：2005-02-03

  Compounds of formula (I) in which R 1 , R 2 and X 4 have the meanings given in the specification are Factor Xa inhibitors useful in the treatment of thrombotic disorders.

  式(I)中R1、R2和X4的含义如说明书所示的化合物是Xa因子抑制剂，可用于治疗血栓性疾病。
• THIAZOLE DERIVATIVE
  申请人：Sato Masakazu

  公开号：US20100216787A1

  公开（公告）日：2010-08-26

  A thiazolylimidazole derivative represented by the formula or a pharmaceutically acceptable salt thereof, and an ALK5 inhibitor, an therapeutic agent for alopecia or a hair growth agent having the above as an active ingredient, wherein: X 1 and X 2 are different from each other and represent a sulfur atom or a carbon atom; R 1 represents a phenyl group; a substituted phenyl group; a phenyl group condensed with a hetero aromatic ring; a pyridyl group; or a pyridyl group condensed with a hetero aromatic ring; R 2 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 5 halogen atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyl group having 1 to 5 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms, A represents a group which is represented by the formula. The present invention provides an inhibitory substance against ALK5 which is a TGF-β type I receptor and provides a hair growth stimulant or a hair growth agent based on its novel activities.

  一种由式表示的噻唑咪唑衍生物或其药学上可接受的盐，并且一种ALK5抑制剂，用作脱发的治疗剂或具有上述物质作为活性成分的生发剂，其中：X1和X2不同且表示硫原子或碳原子；R1表示苯基；取代苯基；与杂环芳香环融合的苯基；吡啶基；或与杂环芳香环融合的吡啶基；R2表示氢原子、卤原子、具有1至6个碳原子的烷基、1至6个碳原子的烷基，其上取代有1至5个卤原子、具有1至6个碳原子的烷氧基、具有1至5个碳原子的烷酰基或具有1至6个碳原子的羟基烷基；A表示由式表示的基团。本发明提供了一种抗ALK5的抑制物质，该物质是一种TGF-β类型I受体，并基于其新的活性提供了一种生发刺激剂或生发剂。
• Precision Synthesis of Polysarcosine via Controlled Ring-Opening Polymerization of <i>N</i>-Carboxyanhydride: Fast Kinetics, Ultrahigh Molecular Weight, and Mechanistic Insights
  作者：Shuo Wang、Ming-Yuan Lu、Si-Kang Wan、Chun-Yan Lyu、Zi-You Tian、Kai Liu、Hua Lu

  DOI：10.1021/jacs.3c14740

  日期：2024.2.28

  rapid and controlled synthesis of high-molecular-weight (HMW) polysarcosine (pSar), a potential polyethylene glycol (PEG) alternative, via the ring-opening polymerization (ROP) of N-carboxyanhydride (NCA) is rare and challenging. Here, we report the well-controlled ROP of sarcosine NCA (Sar-NCA) that is catalyzed by various carboxylic acids, which accelerate the polymerization rate up to 50 times,

  通过N-羧酸酐 (NCA) 的开环聚合 (ROP) 快速、受控合成高分子量 (HMW) 聚肌氨酸 (pSar)（一种潜在的聚乙二醇 (PEG) 替代品）是罕见且具有挑战性的。在这里，我们报道了由各种羧酸催化的肌氨酸NCA（Sar-NCA）的良好控制的ROP，其将聚合速率提高了50倍，并且能够稳健地合成具有前所未有的超高分子量（UHMW）的pSar ) 高达 586 kDa (DP ∼ 8200)，且分散度 ( D̵ ) 极窄，低于 1.05。机理实验和密度泛函理论计算共同阐明了羧酸作为双功能催化剂的作用，可显着促进质子转移过程并避免电荷分离，并表明 NCA 的开环而不是脱羧作为速率决定步骤。 UHMW pSar 表现出比低分子量同类产品更高的热性能和机械性能。这项工作为 UHMW pSar 提供了一种简单而高效的方法，并产生了新的基本理解，不仅对 Sar-NCA 的 ROP 有用，而且对其他