2-(methylamino)-4-nitrophenol | 14703-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(methylamino)-4-nitrophenol
• CAS: 14703-72-1
• 化学式: C₇H₈N₂O₃
• 分子量: 168.152
• InChiKey: OQDUNHRRMXVVFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(methylamino)-4-nitrophenol 在 盐酸 、 sodium hydroxide 、 sodium methylate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 生成 (2S,3S,4S,5R,6S)-6-[2-[[4-[bis(2-chloroethyl)amino]phenoxy]carbonyl-methylamino]-4-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Glucuronide prodrugs of hydroxy compounds for antibody directed enzyme prodrug therapy (ADEPT) : A phenol nitrogen mustard carbamate

  摘要：

  A prodrug consisting of a beta-D-glucuronic acid linked to a self-immolative spacer (a N-(orthohydroxyphenyl)-N-methylcarbamate) and a phenolic nitrogen mustard was synthesised. As this prodrug was easily cleaved by a beta-glucuronidase enzyme and displayed low cytotoxicity, it must be considered as appropriate for an ADEPT approach. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00157-1
• 作为产物：
  描述：

  2-氨基-4-硝基苯酚 在 dimethyl sulfide borane 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 2-(methylamino)-4-nitrophenol
  参考文献：
  名称：

  [EN] GLUCURONIDE PRODRUGS OF TOFACITINIB
  [FR] PROMÉDICAMENTS À BASE DE GLUCURONIDE DE TOFACITINIB

  摘要：

  这项发明涉及具有式(I)的Janus激酶（JAK）抑制剂托法替尼的葡萄糖醛酸酯前药化合物：（式(I)）其中A1和R1如所定义。该发明还涉及包含这种化合物的药物组合物；使用这种化合物治疗胃肠道炎症性疾病的方法；以及制备这种化合物的过程和中间体。

  公开号：

  WO2018165250A1

文献信息

• GLUCURONIDE PRODRUGS OF JANUS KINASE INHIBITORS
  申请人：THERAVANCE BIOPHARMA R&D IP, LLC

  公开号：US20180339990A1

  公开（公告）日：2018-11-29

  The invention relates to glucuronide prodrug compounds of Janus kinase (JAK) inhibitors having formula I: where W 1 , R 1 and A 1 are as defined. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds to treat gastrointestinal inflammatory diseases; and processes and intermediates for preparing such compounds.

  本发明涉及具有公式I的糖苷酸前药化合物的Janus激酶（JAK）抑制剂：其中W1、R1和A1如所定义。本发明还涉及包含这些化合物的药物组合物；使用这些化合物治疗胃肠炎性疾病的方法；以及制备这些化合物的过程和中间体。
• BENZODICYCLOALKANE DERIVATIVE, PREPARATION METHOD AND USE THEREOF
  申请人：SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO., LTD.

  公开号：US20190161468A1

  公开（公告）日：2019-05-30

  It is provided herein a benzobicycloalkane derivative, and a preparation method and use thereof. In particular, it is provided herein a compound of Formula (I), or a pharmaceutically acceptable salt, stereoisomer or solvate thereof, a preparation method, and a use thereof in preparation of drugs for treating pain.

  本文提供了一种苯并螺环烷衍生物，以及其制备方法和用途。具体而言，本文提供了一种式（I）化合物，或其药用可接受的盐、立体异构体或溶剂化合物，以及其制备方法，并用于制备治疗疼痛药物的用途。
• Prodrugs for the therapy of tumors and inflammatory disorders
  申请人：Heochst Aktiengesellschaft

  公开号：US05935995A1

  公开（公告）日：1999-08-10

  Compounds of the formula I glycosyl-Y\x9b--C(.dbd.Y)--X--!.sub.p --W(R).sub.n --Z--C(.dbd.Y)-active compound (I) are described which are suitable for the treatment of carcinomatous diseases, autoimmune diseases and chronic inflammatory diseases such as rheumatoid arthritis.

  化合物的公式I糖基-Y\x9b--C(.dbd.Y)--X--!.sub.p --W(R).sub.n --Z--C(.dbd.Y)-活性化合物（I）适用于治疗癌症性疾病、自身免疫疾病和慢性炎症性疾病，如类风湿性关节炎。
• Synthesis of Novel<i>bis</i>-Phosphonate Derivatives by Pudovik Reaction
  作者：B. Hari Babu、K. Srinivasulu、B. Venu Babu、R. Srinivas、C. Naga Raju

  DOI：10.1080/00397910802005273

  日期：2008.8.18

  Abstract Synthesis of novel bis-(3-methyl-5-nitro-2-oxo-2,3-dihydro-2λ 5benzo[1,3,2]oxazaphosphol-2yl)substituted aryl methanes was accomplished by Pudovik reaction. Addition of equimolar quantities of 2-methylamino-4-nitro phenol (1) and ethanol to PCl3 afforded cyclic condensation product. On reaction with respective aldehydes followed by treatment with phosphorus(III) monochloride of 1, and on subsequent

  摘要 通过Pudovik反应合成了新型双-(3-methyl-5-nitro-2-oxo-2,3-dihydro-2λ 5benzo[1,3,2]oxazaphosphol-2yl)取代芳基甲烷。将等摩尔量的 2-甲氨基-4-硝基苯酚 (1) 和乙醇加入到 PCl3 中，得到环状缩合产物。与相应的醛反应，然后用 1 的一氯化磷 (III) 处理，随后在回流温度下反应，这从 P(III) 重排为 P(V) 状态。它们的结构由 IR、1H NMR、13C NMR、31P NMR 和质谱数据确定。
• Expanding the Substrate Scope of <i>N</i>‐ and <i>O</i>‐Methyltransferases from Plants for Chemoselective Alkylation**
  作者：Emely Jockmann、Fabiana Subrizi、Michael K. F. Mohr、Eve M. Carter、Pia M. Hebecker、Désirée Popadić、Helen C. Hailes、Jennifer N. Andexer

  DOI：10.1002/cctc.202300930

  日期：2023.11.22

  Methylation reactions are of significant interest when generating pharmaceutically active molecules and building blocks for other applications. Synthetic methylating reagents are often toxic and unselective due to their high reactivity. S‐Adenosyl‐l‐methionine (SAM)‐dependent methyltransferases (MTs) present a chemoselective and environmentally friendly alternative. The anthranilate N‐MT from Ruta graveolens (RgANMT) is involved in acridone alkaloid biosynthesis, methylating anthranilate. Although it is known to methylate substrates only at the N‐position, the closest relatives with respect to amino acid sequence similarities of over 60 % are O‐MTs catalysing the methylation reaction of caffeate and derivatives containing only hydroxyl groups (CaOMTs). In this study, we investigated the substrate range of RgANMT and a CaOMT from Prunus persica (PpCaOMT) using compounds with both, an amino‐ and hydroxyl group (aminophenols) as possible methyl group acceptors. For both enzymes, the reaction was highly chemoselective. Furthermore, generating cofactor derivatives in situ enabled the transfer of other alkyl chains onto the aminophenols, leading to an enlarged pool of products. Selected MT reactions were performed at a preparative biocatalytic scale in in vitro and in vivo experiments resulting in yields of up to 62 %.

  摘要 甲基化反应在生成具有医药活性的分子和用于其他应用的构件时具有重要意义。合成甲基化试剂由于反应活性高，通常具有毒性和非选择性。依赖 S-腺苷-l-蛋氨酸（SAM）的甲基转移酶（MTs）提供了一种化学选择性和环境友好型的替代方法。Ruta graveolens 中的蚁酸 N-MT（RgANMT）参与吖啶酮生物碱的生物合成，将蚁酸甲基化。虽然已知它只能在 N 位甲基化底物，但氨基酸序列相似度超过 60% 的近亲是催化咖啡酸酯和仅含羟基的衍生物（CaOMTs）甲基化反应的 O-MTs 。在这项研究中，我们使用同时含有氨基和羟基（氨基苯酚）的化合物作为可能的甲基受体，研究了 RgANMT 和一种来自柿树的 CaOMT（PpCaOMT）的底物范围。这两种酶的反应都具有高度化学选择性。此外，原位生成辅助因子衍生物可以将其他烷基链转移到氨基苯酚上，从而扩大产物库。在体外和体内实验中，以制备生物催化的规模进行了选定的 MT 反应，结果产率高达 62%。