4-氨基-3-((叔丁氧基羰基)氨基)苯甲酸 | 1282523-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基-3-((叔丁氧基羰基)氨基)苯甲酸
• 中文别名: 4-氨基-3-[(叔丁氧羰基)氨基]苯甲酸
• 英文名称: 3-(N-tert-butoxycarbonyl)-3,4-diaminobenzoic acid
• 英文别名: 4-amino-3-(tert-butoxycarbonylamino)benzoic acid；4-Amino-3-((tert-butoxycarbonyl)amino)benzoic acid；4-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]benzoic acid
• CAS: 1282523-83-4
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: IWQZDVMJSKYZEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192 °C
• 沸点：
  378.0±37.0 °C(Predicted)
• 密度：
  1.305

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  4-氨基-3-((叔丁氧基羰基)氨基)苯甲酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-methyl 2-(3,4-diaminobenzamido)-5-guanidinopentanoate
  参考文献：
  名称：

  3,4-Diaminobenzoic Acid Derivatives as Inhibitors of the Oxytocinase Subfamily of M1 Aminopeptidases with Immune-Regulating Properties

  摘要：

  Members of the oxytocinase subfamily of M1 aminopeptidases (ERAP1, ERAP2, and IRAP) play important roles in both the adaptive and innate human immune responses. Their enzymatic activity can contribute to the pathogenesis of several major human diseases ranging from viral and parasitic infections to autoimmunity and cancer. We have previously demonstrated that diaminobenzoic acid derivatives show promise as selective inhibitors for this group of aminopeptidases. In this study, we have thoroughly explored a series of 3,4-diaminobenzoic acid derivatives as inhibitors of this class of enzymes, achieving submicromolar inhibitors for ERAP2 (IC50 = 237 nM) and IRAP (IC50 = 105 nM). Cell-based analysis indicated that the lead compounds can be effective in downregulating macrophage activation induced by lipopolysaccharide and interferon-gamma as well as cross-presentation by bone marrow-derived dendritic cells. Our results indicate that this class of inhibitors may be useful for the targeted downregulation of immune responses.

  DOI：

  10.1021/jm501867s
• 作为产物：
  描述：

  3,4-二氨基苯甲酸甲酯 在 盐酸胍 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 0.67h， 生成 4-氨基-3-((叔丁氧基羰基)氨基)苯甲酸
  参考文献：
  名称：

  3,4-Diaminobenzoic Acid Derivatives as Inhibitors of the Oxytocinase Subfamily of M1 Aminopeptidases with Immune-Regulating Properties

  摘要：

  Members of the oxytocinase subfamily of M1 aminopeptidases (ERAP1, ERAP2, and IRAP) play important roles in both the adaptive and innate human immune responses. Their enzymatic activity can contribute to the pathogenesis of several major human diseases ranging from viral and parasitic infections to autoimmunity and cancer. We have previously demonstrated that diaminobenzoic acid derivatives show promise as selective inhibitors for this group of aminopeptidases. In this study, we have thoroughly explored a series of 3,4-diaminobenzoic acid derivatives as inhibitors of this class of enzymes, achieving submicromolar inhibitors for ERAP2 (IC50 = 237 nM) and IRAP (IC50 = 105 nM). Cell-based analysis indicated that the lead compounds can be effective in downregulating macrophage activation induced by lipopolysaccharide and interferon-gamma as well as cross-presentation by bone marrow-derived dendritic cells. Our results indicate that this class of inhibitors may be useful for the targeted downregulation of immune responses.

  DOI：

  10.1021/jm501867s

文献信息

• LINKER-DRUG AND ANTIBODY-DRUG CONJUGATE (ADC) EMPLOYING THE SAME
  申请人：Industrial Technology Research Institute

  公开号：US20180169262A1

  公开（公告）日：2018-06-21

  A linker-drug represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof is provided. In formula (I), C is a conjugator, L is a linker unit, D is a toxin unit, and n is an integer ranging from 1 to 4. The structure of the conjugator is represented by formula (II). In formula (II), X is a leaving group, each of R 1 and R 2 is independently a single bond or —NH—, and Z is substituted aryl, heteroaryl, linear alkyl, cycloalkyl, heterocycloalkyl, or a combination thereof. The antibody is conjugated to the linker unit through a cysteine residue of the antibody. An antibody-drug conjugate (ADC) employing the above linker-drug is also provided.

  提供由式（I）表示的连接药物或其药学上可接受的盐或溶剂。在式（I）中，C是一个结合物，L是一个连接单元，D是一个毒素单元，n是一个从1到4的整数。结合物的结构由式（II）表示。在式（II）中，X是一个离去基团，R1和R2中的每一个独立地是一个单键或—NH—，Z是取代芳基、杂环芳基、直链烷基、环烷基、杂环烷基或它们的组合。抗体通过抗体的半胱氨酸残基与连接单元结合。还提供了使用上述连接药物的抗体-药物结合物（ADC）。
• REMOVABLE SACCHARIDE-BENZIMIDAZOLE (BIM) TAGS AND CONJUGATES THEREOF VIA 1H-POSITION OF THE BENZIMIDAZOLES
  申请人：YANG Wen-Bin

  公开号：US20130102049A1

  公开（公告）日：2013-04-25

  Novel method and reagents for generating reversibly tagged saccharides, aldehydes, carboxyl acids, or orthoacetates useful in analytical and diagnostic applications are disclosed. Saccharides are coupled at the reducing end to tagging moieties comprising a reagent selected from a ortho-diaminobenzoic(DAB)-peptide, an aldo-imidazole or N-methylated aldo-imidazole, or an ortho-phenyldiamine (OPD) or substituted OPD. The tagged saccharide further comprising detectable or functional groups coupled to the tagging moiety are provided. Kits and reagents for chromatography and mass spectrometry are disclosed.

  揭示了一种用于生成可逆标记的糖类、醛类、羧酸或正乙酸酯的新方法和试剂，这些糖类、醛类、羧酸或正乙酸酯在分析和诊断应用中很有用。将糖类在还原端与标记基团偶联，所述标记基团包括从邻二氨基苯甲酸(DAB)-肽、醛基咪唑或N-甲基化的醛基咪唑，或邻苯二胺(OPD)或取代的OPD中选择的试剂。进一步提供了与标记基团偶联的可检测或功能性基团的标记糖类。还揭示了用于色谱和质谱的试剂盒和试剂。
• Linker-drug and antibody-drug conjugate (ADC) employing the same
  申请人：Industrial Technology Research Institute

  公开号：US10864279B2

  公开（公告）日：2020-12-15

  A linker-drug represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof is provided. In formula (I), C is a conjugator, L is a linker unit, D is a toxin unit, and n is an integer ranging from 1 to 4. The structure of the conjugator is represented by formula (II). In formula (II), X is a leaving group, each of R1 and R2 is independently a single bond or —NH—, and Z is substituted aryl, heteroaryl, linear alkyl, cycloalkyl, heterocycloalkyl, or a combination thereof. The antibody is conjugated to the linker unit through a cysteine residue of the antibody. An antibody-drug conjugate (ADC) employing the above linker-drug is also provided.

  本发明提供了一种由式（I）表示的连接剂-药物或其药学上可接受的盐或溶液。在式 (I) 中，C 是共轭物，L 是连接体单元，D 是毒素单元，n 是 1 至 4 的整数。在式 (II) 中，X 是离去基团，R1 和 R2 各自独立地是单键或-NH-，Z 是取代的芳基、杂芳基、直链烷基、环烷基、杂环烷基或它们的组合。抗体通过抗体的半胱氨酸残基与连接体单元连接。还提供了一种采用上述连接体-药物的抗体-药物共轭物（ADC）。
• Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups
  作者：Fatemeh Jahani、Mahmood Tajbakhsh、Hamid Golchoubian、Samad Khaksar

  DOI：10.1016/j.tetlet.2011.01.023

  日期：2011.3

  A simple and efficient method for the chemoselective N-Boc protection of the amine moiety in a variety of compounds is described using di-tert-butyl dicarbonate and guanidine hydrochloride as an organocatalyst in ethanol at 35-40 degrees C. Selective mono-N-Boc protection of diamines and chemoselective protection of hydroxylamines without formation of any side products is achieved. Amino acids and peptides are N-Boc protected efficiently in excellent yields under convenient reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• US9086416B2
  申请人：——

  公开号：US9086416B2

  公开（公告）日：2015-07-21