4-[N-Boc-N-(pyridin-2-ylmethyl)aminomethyl]benzoic acid | 369654-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[N-Boc-N-(pyridin-2-ylmethyl)aminomethyl]benzoic acid
• 英文别名: 4-(N-Boc-N-2-picolylaminomethyl) benzoic acid；4-(N-Boc-N-2-picolylaminomethyl)benzoic acid；4-[[(2-methylpropan-2-yl)oxycarbonyl-(pyridin-2-ylmethyl)amino]methyl]benzoic acid
• CAS: 369654-36-4
• 化学式: C₁₉H₂₂N₂O₄
• 分子量: 342.395
• InChiKey: VUXQYHCMESMEKT-UHFFFAOYSA-N

物化性质

• 沸点：
  514.9±50.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[N-Boc-N-(pyridin-2-ylmethyl)aminomethyl]benzoic acid 、 Fmoc-Orn(Boc)-OMe 在 二乙胺 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 26.0h， 生成 Nα-(4-(N-Boc-N-(2-picolyl)aminomethyl)benzoyl)-Nδ-Boc-L-ornithinemethylester
  参考文献：
  名称：

  CXCR4-ANTAGONISTIC DRUGS COMPRISING NITROGEN-CONTAINING COMPOUND

  摘要：

  为基于CXCR4拮抗作用提供对CXCR4具有拮抗作用的新型含氮化合物和治疗风湿病、癌症转移等疾病的药物。以下是一般式代表的含氮化合物和以这些化合物为活性成分的CXCR4拮抗剂。上述化合物以以下一般式（I）代表的含氮化合物为代表，其中A1和A2分别代表鸟氨基基团或由以下一般式（ia）代表的基团（其中A3代表具有1个或2个杂原子的单环或多环杂环芳香环基团；B1代表单键或烷基基团；R1代表氢或烷基基团；W代表具有2至3个碳原子的烷基基团、具有5至10个碳原子的环烷基团、具有6至10个碳原子的芳香环或具有5至10个碳原子的杂环芳香环；y为-(C=O)-；x为-C(=O)-NH-；n1为1或2的整数；n2为2或3的整数；D从各种取代基中选择）。

  公开号：

  EP1389460A1
• 作为产物：
  描述：

  N-BOC-2-氨甲基吡啶 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[N-Boc-N-(pyridin-2-ylmethyl)aminomethyl]benzoic acid
  参考文献：
  名称：

  Probing the Molecular Interactions between CXC Chemokine Receptor 4 (CXCR4) and an Arginine-Based Tripeptidomimetic Antagonist (KRH-1636)

  摘要：

  We here report an experimentally verified binding mode for the known tripeptidomimetic CXCR4 antagonist KRH-1636 (1). A limited SAR study based on the three functionalities of 1 was first conducted, followed by site-directed mutagenesis studies. The receptor mapping showed that both the potency and affinity of 1 were dependent on the transmembrane residues His(113), Asp(171), Asp(262), and His(281) and also suggested the involvement of Tyr(45) and Gln(200). (potency) and Tyr(116) and Glu(288) (affinity). Molecular docking of 1 to an X-ray structure of CXCR4 showed that the L-Arg guanidino group of 1 forms polar interactions with His(113) and Asp(171) and the (pyridin-2-ylmethyl)amino moiety is anchored by Asp(262) and His(281), whereas the naphthalene ring is tightly packed in a hydrophobic subpocket formed by the aromatic side chains of Trp(94), Tyr(45), and Tyr(116). The detailed picture of ligand-receptor interactions provided here will assist in structure-based design and further development of small-molecule peptidomimetic CXCR4 antagonists.

  DOI：

  10.1021/acs.jmedchem.5b00987

文献信息

• NOVEL NITROGENOUS COMPOUND AND USE THEREOF
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP1431290A1

  公开（公告）日：2004-06-23

  A novel nitrogen-containing compound effective against diseases such as HIV viral infectious diseases, rheumatism, and cancerous metastasis. It is a nitrogen-containing compound represented by the following general formula (1). In the formula, A typically represents a group represented by the formula (2) (A1 is hydrogen or an optionally substituted, mono- or polycyclic, heteroaromatic or aromatic ring; G1 is a single bond or a hydrocarbon group represented by the following formula (3) wherein R1, R2, and R3 may be optionally substituted hydrocarbon groups); W is an optionally substituted hydrocarbon group or heterocyclic ring; x is -C(=O)NH-; y is -C(=O)-; and D1 is hydrogen atom, alkyl having a polycyclic aromatic ring, di (substituted alkyl)amine, or alicyclic amine.

  一种新型含氮化合物，对HIV病毒感染性疾病、风湿病和癌细胞转移等疾病具有有效作用。它是一种由下述通用式(1)表示的含氮化合物。在该式中，A通常表示由式(2)表示的基团（A1是氢或可选择取代的单环或多环杂环芳香环；G1是单键或由下述式(3)表示的碳氢基团，其中R1、R2和R3可能是可选择取代的碳氢基团）；W是可选择取代的碳氢基团或杂环环；x是-C(=O)NH-；y是-C(=O)-；D1是氢原子、具有多环芳香环的烷基、二（取代烷基）胺或脂环胺。
• NITROGENOUS COMPOUNDS AND ANTIVIRAL DRUGS CONTAINING THE SAME
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP1273571A1

  公开（公告）日：2003-01-08

  The present invention provides novel compounds having antiviral activities and antiviral drugs containing the compounds as the active ingredient. The compounds are shown by the following general formula (1), wherein typically A1 and A2 are each guanidine or a group of the general fomula (ia) ; A3 is a mono- or poly-cyclic heteroaromatic ring contining 1 or 2 heteroatoms ; B1 is a single bond or alkylene group; R1 is hydrogen or alkyl group; W is an alkylene having 2-3 carbons, a cycloalkylene having 5-10 carbons, aromatic ring having 6-10 carbons, or a heteroaromatic ring having 5-10 carbons; y is C(=O)-; x is -C(=O)-NH-; n1 is an integer of 1-2; n2 is an integer of 2-3; D is a substituent selected from among various groups.

  本发明提供了具有抗病毒活性的新化合物以及含有这些化合物作为活性成分的抗病毒药物。这些化合物由以下一般式（1）所示，其中通常A1和A2分别是胍或一般式（ia）的基团；A3是含有1个或2个杂原子的单环或多环杂芳环；B1是单键或烷基基团；R1是氢或烷基基团；W是具有2-3个碳的烷基、具有5-10个碳的环烷基、具有6-10个碳的芳香环或具有5-10个碳的杂芳环；y是C(=O)-；x是-C(=O)-NH-；n1是1-2的整数；n2是2-3的整数；D是从各种基团中选择的取代基。
• Nitrogenous compounds and antiviral drugs containing the same
  申请人：——

  公开号：US20040092556A1

  公开（公告）日：2004-05-13

  The present invention provides novel compounds having antiviral activities and antiviral drugs containing the compounds as the active ingredient. The compounds are shown by the following general formula (1), wherein typically A 1 and A 2 are each guanidine or a group of the general fomula (ia); A 3 is a mono- or poly-cyclic heteroaromatic ring contining 1 or 2 heteroatoms; B 1 is a single bond or alkylene group; R 1 is hydrogen or alkyl group; W is an alkylene having 2-3 carbons, a cycloalkylene having 5-10 carbons, aromatic ring having 6-10 carbons, or a heteroaromatic ring having 5-10 carbons; y is C(═O)—; x is —C(═O)—NH—; n 1 is an integer of 1-2; n 2 is an integer of 2-3; D is a substituent selected from among various groups. 1

  本发明提供了具有抗病毒活性的新化合物和包含该化合物作为活性成分的抗病毒药物。该化合物由以下通式（1）表示，其中通常A1和A2分别是鸟氨酸或通式（ia）的基团；A3是含有1或2个杂原子的单环或多环杂芳基环；B1是单键或烷基链；R1是氢或烷基基团；W是具有2-3个碳的烷基，具有5-10个碳的环烷基，具有6-10个碳的芳环基或具有5-10个碳的杂芳基环；y是C（═O）-；x是-C（═O）-NH-；n1是1-2的整数；n2是2-3的整数；D是从各种基团中选择的取代基。
• Novel Nitrogenous Compound and use thereof
  申请人：——

  公开号：US20040254221A1

  公开（公告）日：2004-12-16

  A novel nitrogen-containing compound effective against diseases such as HIV viral infectious diseases, rheumatism, and cancerous metastasis. It is a nitrogen-containing compound represented by the following general formula (1). In the formula, A typically represents a group represented by the formula (2) (A 1 is hydrogen or an optionally substituted, mono- or polycyclic, heteroaromatic or aromatic ring; G 1 is a single bond or a hydrocarbon group represented by the following formula (3) wherein R 1 , R 2 , and R 3 may be optionally substituted hydrocarbon groups); W is an optionally substituted hydrocarbon group or heterocyclic ring; x is —C(═O)NH—; y is —C(═O)—; and D 1 is hydrogen atom, alkyl having a polycyclic aromatic ring, di(substituted alkyl)amine, or alicyclic amine. 1

  一种新型的含氮化合物，对HIV病毒感染性疾病、风湿病和癌症转移等疾病有效。它是一种含氮化合物，通常由以下一般式（1）表示。在该式中，A通常表示由式（2）表示的基团（其中A1是氢原子或可选地取代的单环或多环杂环芳香环或芳香环；G1是单键或由以下式（3）表示的烃基，其中R1、R2和R3可能是可选地取代的烃基）；W是可选地取代的烃基或杂环环；x是—C(═O)NH—；y是—C(═O)—；D1是氢原子、具有多环芳香环的烷基、二（取代烷基）胺或脂环胺。
• Chemical Compounds
  申请人：Gudmundsson Kristjan

  公开号：US20080096861A1

  公开（公告）日：2008-04-24

  The present invention provides compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind to chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 of a target cell.

  本发明提供了一种化合物，它以结合趋化因子受体的方式对目标细胞表现出对HIV感染的保护作用，并且影响天然配体或趋化因子与目标细胞的CXCR4等受体的结合。