5-氨基-1-甲氧基异喹啉 | 72678-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 5-氨基-1-甲氧基异喹啉
• 英文名称: 5-amino-1-methoxyisoquinoline
• 英文别名: 5-Amino-1-methoxy-isochinolin；1-methoxy-isoquinolin-5-ylamine；1-Methoxy-5-isoquinolinamine；1-Methoxyisoquinolin-5-amine
• CAS: 72678-02-5
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: WMABIBWLZLPHKF-UHFFFAOYSA-N

物化性质

• 沸点：
  346.6±27.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氨基-1-甲氧基异喹啉 在 copper(l) iodide 、 铜 N-乙基吗啉 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 3.0h， 生成 4-Methoxy-3,7,12-triaza-benzo[a]anthracene-11-carboxylic acid ((R)-2-dimethylamino-1-methyl-ethyl)-amide
  参考文献：
  名称：

  Structure−Activity Relationships for Pyrido-, Imidazo-, Pyrazolo-, Pyrazino-, and Pyrrolophenazinecarboxamides as Topoisomerase-Targeted Anticancer Agents

  摘要：

  Heterocyclic phenazinecarboxamides were prepared by condensation of aminoheterocycles and 2-halo-3-nitrobenzoic acids, followed by reductive ring closure and amidation. They showed similar inhibition of paired cell lines that underexpressed topo II or overexpressed P-glycoprotein, indicating a non topo II mechanism of cytotoxicity and indifference to P-glycoprotein mediated multidrug resistance. Compounds with a fused five-membered heterocyclic ring were generally less potent than the pyrido[4,3-alpha]phenazines. A 4-methoxypyrido[4,3-alpha]phenazine (IC(50)s 2.5-26 nM) gave modest (ca. 5 day) growth delays in H69/P xenografts with oral dosing.

  DOI：

  10.1021/jm010330+
• 作为产物：
  描述：

  1-氯异喹啉 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 potassium nitrate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 5-氨基-1-甲氧基异喹啉
  参考文献：
  名称：

  Structure−Activity Relationships for Pyrido-, Imidazo-, Pyrazolo-, Pyrazino-, and Pyrrolophenazinecarboxamides as Topoisomerase-Targeted Anticancer Agents

  摘要：

  Heterocyclic phenazinecarboxamides were prepared by condensation of aminoheterocycles and 2-halo-3-nitrobenzoic acids, followed by reductive ring closure and amidation. They showed similar inhibition of paired cell lines that underexpressed topo II or overexpressed P-glycoprotein, indicating a non topo II mechanism of cytotoxicity and indifference to P-glycoprotein mediated multidrug resistance. Compounds with a fused five-membered heterocyclic ring were generally less potent than the pyrido[4,3-alpha]phenazines. A 4-methoxypyrido[4,3-alpha]phenazine (IC(50)s 2.5-26 nM) gave modest (ca. 5 day) growth delays in H69/P xenografts with oral dosing.

  DOI：

  10.1021/jm010330+

文献信息

• Substituted dihydroisoquinolinones and related compounds as potentiators
  申请人：Warner-Lambert Company

  公开号：US05177075A1

  公开（公告）日：1993-01-05

  The invention is selected, novel, and known analogs of isoquinolinones of the formula ##STR1## and pharmaceutically acceptable salts thereof; novel pharmaceutical compositions; and a method for enhancing the lethal effects for tumor cells to treatment having DNA damaging activity such as ionizing radiation or with chemotherapeutic agents.

  这项发明涉及选择的、新颖的、以及已知的异喹啉酮类化合物及其药学上可接受的盐；新颖的药物组合物；以及一种增强对肿瘤细胞的致命效应的方法，该方法包括对具有DNA损伤活性的治疗方法进行增强，例如电离辐射或化疗药物。
• Pharmaceutical compounds
  申请人：——

  公开号：US20010034346A1

  公开（公告）日：2001-10-25

  A compound which is a heteroaromatic[a]phenazine carboxamide derivative of formula (I) 1 wherein X is a five- or six-membered heteroaromatic ring which contains one or two nitrogen atoms and which is unsubstituted or substituted by C 1 -C 6 alkyl, hydroxyl or C 1 -C 6 alkoxy; Q is C 1 -C 6 alkylene which is unsubstituted or substituted by C 1 -C 6 alkyl which is unsubstituted or substituted by a hydroxy group; and R 1 and R 2 which are the same or different are each C 1 -C 6 alkyl; or a pharmaceutically acceptable salt thereof. These compounds are inhibitors of topoisomerase I and II and can be used to treat tumours, including tumours which express MDR.

  该化合物是公式（I）的杂环芳香基苯并吡嗪羧酰胺衍生物，其中X是一个含有一个或两个氮原子的五元或六元杂环芳香环，未取代或取代为C1-C6烷基，羟基或C1-C6烷氧基; Q是未取代或取代为C1-C6烷基（未取代或取代为羟基基团）的C1-C6烷基; R1和R2相同或不同，均为C1-C6烷基; 或其药学上可接受的盐。这些化合物是拓扑异构酶I和II的抑制剂，并可用于治疗肿瘤，包括表达MDR的肿瘤。
• 1,2,4-TRIAZINE-6-CARBOXAMIDE DERIVATIVE
  申请人：Taiho Pharmaceutical Co., Ltd.

  公开号：EP2762476A1

  公开（公告）日：2014-08-06

  The present invention provides a compound represented by the following general formula (I) or a salt thereof which has a Syk inhibitory effect (in the formula R1 represents a hydrogen atom or an optionally Ra-substituted C1-C6 alkyl group; A represents a hydrogen atom, an optionally Ra-substituted C1-C8 alkyl group, an optionally Ra-substituted C2-C6 alkenyl group, an optionally Ra-substituted C2-C6 alkynyl group, an optionally Rb-substituted C3-C10 cycloalkyl group, an optionally Rb-substituted C6-C14 aromatic hydrocarbon group, an optionally Rb-substituted 4- to 10-membered unsaturated heterocyclic group, or an optionally Rb-substituted 4-to 10-membered saturated heterocyclic group, or optionally forms a 4- to 10-membered unsaturated heterocyclic ring or a 4- to 10-membered saturated heterocyclic ring together with R1 and the nitrogen atom bonded thereto; R2 represents a hydrogen atom or an optionally Ra-substituted C1-C6 alkyl group; and B represents an optionally Rc-substituted unsaturated heterocyclic group).

  本发明提供了由下通式（I）代表的化合物或其盐，该化合物具有抑制 Syk 的作用（式中 R1 代表氢原子或任选 Ra 取代的 C1-C6 烷基；A代表氢原子、任选Ra取代的C1-C8烷基、任选Ra取代的C2-C6烯基、任选Ra取代的C2-C6炔基、任选Rb取代的C3-C10环烷基、任选Rb取代的C6-C14芳烃基、任选 Rb 取代的 4 至 10 元不饱和杂环基团，或任选 Rb 取代的 4 至 10 元饱和杂环基团，或任选与 R1 及其键合的氮原子一起形成 4 至 10 元不饱和杂环或 4 至 10 元饱和杂环；R2 代表氢原子或任选 Ra 取代的 C1-C6 烷基；以及 B 代表任选 Rc 取代的不饱和杂环基团）。
• TABLETS CONTAINING 4,6-DIAMINO-QUINOLINE-3-CARBONITRILE DERIVATIVES AS CANCER OSAKA THYROID (COT) MODULATORS FOR TREATING CANCER
  申请人：GILEAD SCIENCES, INC.

  公开号：EP3456717A1

  公开（公告）日：2019-03-20

  Tablets containing 4,6-diamino-quinoline-3-carbonitrile derivatives as cancer Osaka thyroid (COT) modulators for treating cancer.

  含有 4,6-二氨基-喹啉-3-甲腈衍生物的片剂，作为治疗癌症的大阪甲状腺（COT）调节剂。
• 4,6-DIAMINO-QUINOLINE-3-CARBONITRILE DERIVATIVES AS CANCER OSAKA THYROID (COT) MODULATORS FOR TREATING CROHN'S DISEASE AND ULCERATIVE COLITIS
  申请人：Gilead Sciences, Inc.

  公开号：EP3896064A1

  公开（公告）日：2021-10-20

  The present disclosure relates to 4,6-diamino-quinoline-3-carbonitrile derivatives for use as modulators of COT (Cancer Osaka Thyroid) in methods of treating Crohn's disease and ulcerative colitis.

  本公开涉及在治疗克罗恩病和溃疡性结肠炎的方法中用作 COT（癌症大阪甲状腺）调节剂的 4,6-二氨基-喹啉-3-甲腈衍生物。