2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)-amino)acetic acid | 158979-29-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: 2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)-amino)acetic acid
• 英文别名: 2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)amino)acetic acid；2-((t-butoxycarbonyl)(prop-2-yn-1-yl)amino)acetic acid；2-(tert-butoxycarbonyl(prop-2-ynyl)amino)acetic acid；2-[tert-butoxycarbonyl(prop-2-ynyl)amino]acetic acid；N-(tert-butoxycarbonyl)-N-(prop-2-yn-1-yl)glycine；Boc-(prop-2-yne-1-yl)-Gly-OH；[(tert-Butoxycarbonyl)(2-propynyl)amino]acetic acid；2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-ynylamino]acetic acid
• CAS: 158979-29-4
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: UFIXSVLNUUDLSE-UHFFFAOYSA-N

物化性质

• 沸点：
  324.0±35.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)-amino)acetic acid 在 四氯化碳 、 正丁基锂 、 溴 、 1-丙基磷酸酐 、 三乙胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 20.53h， 生成 (2-(3,4-dimethylphenyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)(pyrazin-2-yl)methanone
  参考文献：
  名称：

  Discovery and Characterization of VU0529331, a Synthetic Small-Molecule Activator of Homomeric G Protein-Gated, Inwardly Rectifying, Potassium (GIRK) Channels

  摘要：

  G protein-gated, inwardly rectifying, potassium (GIRK) channels are important regulators of cellular excitability throughout the body. GIRK channels are heterotetrameric and homotetrameric combinations of the K(ir)3.1-4 (GIRK1-4) subunits. Different subunit combinations are expressed throughout the central nervous system (CNS) and the periphery, and most of these combinations contain a GIRK1 subunit. For example, the predominance of GIRK channels in the CNS are composed of GIRK1 and GIRK2 subunits, while the GIRK channels in cardiac atrial myocytes are made up mostly of GIRK1 and GIRK4 subunits. Although the vast majority of GIRK channels contain a GIRK1 subunit, discrete populations of cells that express non-GIRK1-containing GIRK (non-GIRK1/X) channels do exist. For instance, dopaminergic neurons in the ventral tegmental area of the brain, associated with addiction and reward, do not express the GIRK1 subunit. Targeting these non-GIRK1/X channels with subunit-selective pharmacological probes could lead to important insights into how GIRK channels are involved in reward and addiction. Such insights may, in turn, reveal therapeutic opportunities for the treatment or prevention of addiction. Previously, our laboratory discovered small molecules that can specifically modulate the activity of GIRK1-containing GIRK channels. However, efforts to generate compounds active on non-GIRK1/X channels from these scaffolds have been unsuccessful. Recently, ivermectin was shown to modulate non-GIRK1/X channels, and historically, ivermectin is known to modulate a wide variety of neuronal channels and receptors. Further, ivermectin is a complex natural product, which makes it a challenging starting point for development of more selective, effective, and potent compounds. Thus, while ivermectin provides proof-of-concept as a non-GIRK1/X channel activator, it is of limited utility. Therefore, we sought to discover a synthetic small molecule that would serve as a starting point for the development of non-GIRK1/X channel modulators. To accomplish this, we used a high-throughput thallium flux assay to screen a 100 000-compound library in search of activators of homomeric GIRK2 channels. Using this approach, we discovered VU0529331, the first synthetic small molecule reported to activate non-GIRK1/X channels, to our knowledge. This discovery represents the first step toward developing potent and selective non-GIRK1/X channel probes. Such molecules will help elucidate the role of GIRK channels in addiction, potentially establishing a foundation for future development of therapies utilizing targeted GIRK channel modulation.

  DOI：

  10.1021/acschemneuro.8b00287
• 作为产物：
  描述：

  BOC-甘氨酸 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 、 甲苯 为溶剂， 反应 1.6h， 以87%的产率得到2-((tert-butoxycarbonyl)(prop-2-yn-1-yl)-amino)acetic acid
  参考文献：
  名称：

  分子内腈亚胺环加成反应合成取代的2,4,5,6-四氢环戊[ c ]吡唑和2,4,5,6-四氢吡咯并[3,4- c ]吡唑

  摘要：

  取代的2,4,5,6-四氢环戊[ c ]吡唑和2,4,5,6-四氢吡咯并[3,4- c ]吡唑是通过亚硝胺的3 + 2分子内偶极环加成反应而合成的。通过使用炔基溴化物作为亲双性体，这种环化作用已扩展为更通用的3-溴衍生物。

  DOI：

  10.1016/j.tetlet.2014.02.068

文献信息

• Design, Synthesis, and Reactivity of Multidentate Ligands with Rhenium(I) and Rhenium(V) Cores
  作者：Jin‐Hui Wang、Romain Eychenne、Mariusz Wolff、Sonia Mallet‐Ladeira、Nicolas Lepareur、Eric Benoist

  DOI：10.1002/ejic.201700632

  日期：2017.9.8

  functionalized N-((1-(4-R)-1H-1,2,3-triazol-4-yl)methyl)-2-(pyridin-2-ylmethoxy)aniline derivatives L1H (R = methyl acetate) and L2H (R = 4-nitrophenyl) act exclusively as bidentate ligands and lead to the formation of mononuclear tricarbonylrhenium(I) complexes of general formula [(LH)Re(CO)3Cl] with L = L1 or L2. Both complexes are characterized by 1H and 13C NMR, FT-IR spectroscopy, electrospray ionization

  研究了一系列潜在的 N3O 四齿配体的合成途径，旨在协调铼核以及它们对不同铼核（氧化态 +I 和 +V）的配位行为。两种官能化的 N-((1-(4-R)-1H-1,2,3-triazol-4-yl)methyl)-2-(pyridin-2-ylmethoxy)aniline 衍生物 L1H（R = 乙酸甲酯）和L2H（R = 4-硝基苯基）仅用作双齿配体，并导致形成通式 [(LH)Re(CO)3Cl] 的单核三羰基铼 (I) 配合物，其中 L = L1 或 L2。两种配合物均通过 1H 和 13C NMR、FT-IR 光谱、电喷雾电离质谱和 [(L2H)Re(CO)3Cl] 单晶 X 射线衍射研究进行表征。铼由三个羰基配位，三唑的氯和两个氮原子以及配体苯胺环的氮原子。理论研究表明复合物 [(L2H)Re(CO)3Cl] 是最稳定的结构异构体。此外，在 Re(V) 前体 [ReOCl3(PPh3)2]
• Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins
  作者：Paul Dockerty、Jerre G. Edens、Menno B. Tol、Danae Morales Angeles、Arnau Domenech、Yun Liu、Anna K. H. Hirsch、Jan-Willem Veening、Dirk-Jan Scheffers、Martin D. Witte

  DOI：10.1039/c6ob01664b

  日期：——

  Natural products form attractive leads for the development of chemical probes and drugs. The antibacterial lipopeptide Brabantamide A contains an unusual enol cyclocarbamate and we used this scaffold as inspiration for the synthesis of a panel of enol cyclocarbamate containing compounds. By equipping the scaffold with different groups, we identified structural features that are essential for antibacterial

  天然产品为化学探针和药物的开发提供了诱人的线索。抗菌脂肽Brabantamide A包含一种不寻常的烯醇环氨基甲酸酯，我们以此支架为灵感来合成一组包含烯醇环氨基甲酸酯的化合物。通过为脚手架配备不同的组，我们确定了抗菌活性必不可少的结构特征。一些衍生物阻止羟基香豆素羧酸-氨基D-丙氨酸掺入新合成的肽聚糖中。基于活动的蛋白谱分析实验表明，烯醇氨基甲酸酯抑制枯草芽孢杆菌和肺炎链球菌中青霉素结合蛋白的特定子集。
• [EN] PYRROLOPYRAZOLES AS N-TYPE CALCIUM CHANNEL BLOCKERS<br/>[FR] PYRROLOPYRAZOLES COMME BLOQUEURS DE CANAL CALCIQUE DE TYPE N
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2014028805A1

  公开（公告）日：2014-02-20

  Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds are represented by Formula I as follows: Formula. (I) wherein R1, R2 R3, Q, and G are defined herein.

  揭示了用于治疗各种疾病、综合症、症状和障碍的化合物、组合物和方法，包括疼痛。这些化合物由以下的化学式I表示：化学式（I），其中R1、R2、R3、Q和G在此处被定义。
• Synthesis of Specific Bivalent Probes That Functionally Interact with 5-HT₄ Receptor Dimers
  作者：Olivier Russo、Magali Berthouze、Mireille Giner、Jean-Louis Soulier、Lucie Rivail、Sames Sicsic、Frank Lezoualc'h、Ralf Jockers、Isabelle Berque-Bestel

  DOI：10.1021/jm070552t

  日期：2007.9.1

  G-protein-coupled receptor dimerization directs the design of new drugs that specifically bind to receptor dimers. Here, we generated a targeted series of homobivalent ligands for serotonin 5-HT(4) receptor (5-HT(4)R) dimers composed of two 5-HT(4)R-specific ML10302 units linked by a spacer. The design of spacers was assisted by molecular modeling using our previously described 5-HT(4)R dimer model.

  G蛋白偶联受体二聚体指导了特异性结合受体二聚体的新药的设计。在这里，我们针对5-羟色胺5-HT（4）受体（5-HT（4）R）二聚体生成了一系列针对性的同二价配体，该二聚体由两个通过间隔子连接的5-HT（4）R特异性ML10302单元组成。使用我们之前描述的5-HT（4）R二聚体模型，通过分子建模来辅助间隔基的设计。它们的合成基于Sonogashira-Linstrumelle偶联方法。所有化合物保留与5-HT（4）R的高亲和力结合，但失去了单体ML10302化合物的激动特性。使用基于生物发光共振能量转移（BRET）的检测方法，可监测5-HT（4）二聚体中的构象变化，从而获得二价配体与5-HT（4）R的两个药效基团之间功能相互作用的直接证据。尽管一价ML10302在此测定中无活性，但几种二价衍生物剂量依赖性地增加了BRET信号，表明这两个药效团在功能上与5-HT（4）二聚体相互作用。这些二价
• N-substituted peptidyl nitriles as cysteine cathepsin inhibitors
  申请人：——

  公开号：US20030158256A1

  公开（公告）日：2003-08-21

  Compounds of the formula (I), wherein R 1 is aryl or biaryl; R 2 is aryl-lower alkyl, biaryl-lower alkyl, benzo-fused cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C 2 -C 7 -alkyl in which C 2 -C 7 -alkyl is interrupted by Y; Y is O, S, SO, SO 2 , CO or NR 6 ; R 3 is hydrogen or lower alkyl; or R 2 and R 3 combined are C 2 -C 7 -alkylene or C 2 -C 7 -alkylene interrupted by Y; R 4 is hydrogen or lower alkyl; R 5 is hydrogen, optionally substituted lower alkyl, aryl-lower alkyl, biaryl-lower alkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, aryloxy-lower alkyl, or aryl-C 2 -C 7 -alkyl in which C 2 -C 7 -alkyl is interrupted by Y; R 6 is hydrogen, lower alkyl or aryl-lower alkyl; and pharmaceutically acceptable salts thereof, which are useful as cysteine cathepsin inhibitors.

  式（I）的化合物，其中R1是芳基或联苯基；R2是芳基-较低烷基，联苯基-较低烷基，苯并环烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；Y是O，S，SO，SO2，CO或NR6；R3是氢或较低烷基；或R2和R3结合形成C2-C7-烷基或C2-C7-烷基被Y中断；R4是氢或较低烷基；R5是氢，可选择取代的较低烷基，芳基-较低烷基，联苯基-较低烷基，环烷基-较低烷基，双环烷基-较低烷基，芳氧基-较低烷基，或芳基-C2-C7-烷基，其中C2-C7-烷基被Y中断；R6是氢，较低烷基或芳基-较低烷基；及其药学上可接受的盐，可用作半胱氨酸蛋白酶抑制剂。