4-苯胺-1-羟基苯 | 91300-60-6

• 物质功能分类: 生物 - 生化试剂盒
• 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: 4-苯胺-1-羟基苯
• 中文别名: 氯嘧磺隆
• 英文名称: 6-anilinoquinoline-5,8-quinone
• 英文别名: 6-Anilino-5,8-quinolinedione；6-anilinoquinoline-5,8-dione
• CAS: 91300-60-6
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: GXIJYWUWLNHKNW-UHFFFAOYSA-N

物化性质

• 熔点：
  184-185°C
• 沸点：
  446.9±45.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)
• 溶解度：
  0.1MHCl：1 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R40
• WGK Germany：
  2
• 海关编码：
  2933499090
• 安全说明：
  S36/37
• 储存条件：
  2-8°C冷藏

制备方法与用途

用途

该物质以剂量依赖性和可逆的方式抑制一氧化氮诱导的可溶性鸟苷酸环化酶激活（IC50=2μM），并阻断乙酰胆碱引起的血管松弛。同时，它也是抗原诱导的白三烯释放的抑制剂。

反应信息

• 作为反应物：
  描述：

  盐酸 、 4-苯胺-1-羟基苯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5,8-喹啉二酮 、 苯胺
  参考文献：
  名称：

  Fischer,O.; Renouf, Chemische Berichte, 1884, vol. 17, p. 1645

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氨基-8-羟基喹啉 在 potassium dichromate 、 乙醇 、 硫酸 作用下， 生成 4-苯胺-1-羟基苯
  参考文献：
  名称：

  Fischer,O.; Renouf, Chemische Berichte, 1884, vol. 17, p. 1645

  摘要：

  DOI：

文献信息

• DERMATOLOGICAL COMPOSITIONS AND METHODS
  申请人：——

  公开号：US20020141952A1

  公开（公告）日：2002-10-03

  Disclosed are methods and compositions for regulating the melanin content of mammalian melanocytes; regulating pigmentation in mammalian skin, hair, wool or fur; treating or preventing various skin and proliferative disorders; by administration of various compounds, including alcohols, diols and/or triols and their analogues.

  公开了用于调节哺乳动物黑素细胞的黑色素含量的方法及组合物；通过施用包括醇、二醇和/或三醇及其类似物在内的各种化合物，来调节哺乳动物皮肤、毛发、羊毛或毛皮的色素沉着；以及治疗或预防各种皮肤和增殖性障碍。
• Gold(III)-Catalyzed 1,4-Nucleophilic Addition: Facile Approach to Prepare 2-Amino-1,4-naphthalenedione and 6-Amino-5,8-quinolinedione Derivatives
  作者：Shaozhong Wang、Chunhui Jiang

  DOI：10.1055/s-0028-1088116

  日期：2009.4

  An efficient approach is developed to prepare different 2-amino-1,4-naphthalenedione and 6-amino-5,8-quinolinedione derivatives regioselectively by Au(III)-catalyzed 1,4-nucleophilic addition and subsequent oxidation. A wide variety of primary, secondary, and aromatic amines, as well as allylamine and 2-butynyl­amine are well tolerated under the mild conditions to give products in moderate to good yields.

  开发了一种高效的方法，通过金(III)催化的1,4-亲核加成和随后的氧化反应，有选择性地制备不同的2-氨基-1,4-萘二酮和6-氨基-5,8-喹啉二酮衍生物。在温和条件下，多种一级、二级和芳香胺，以及烯丙胺和2-丁炔基胺均能很好地耐受，产物收率中等至良好。
• Compound capable of cytoskeleton and induction of cell elongation and process for synthesizing the same
  申请人：Chao Jui-I

  公开号：US20080015221A1

  公开（公告）日：2008-01-17

  A compound capable of cytoskeleton and induction of cell elongation, 7-chloro-6-piperidin-1-yl-quinoline-5,8-dione with a chemical formula of C 14 H 13 CIN 2 O 2 , is designated as PT-262. The PT-262 can induce cell elongation by stabilization of the F-actin and induction of the abnormal actin polymerization in cancer cells, further, the PT-262 possesses antitumor activity and can block survival pathway of the cancer cells, resulting in cancer cells apoptosis, and the PT-262 can induce growth arrest and inhibition of cell cycle. PT-262 stabilizes cancer cells cytoskeleton that results in an irreversible cell elongation, decreases the levels of cyclin B1 and phospho-cdc2 proteins, and inhibits the survival signal pathway of Ras-ERK proteins. The PT-262 also inhibits the mitochondrial membrane potential and induces the caspase-3 activation and apoptosis in the cancer cells.

  一种具有细胞骨架和诱导细胞延长能力的化合物，化学式为C14H13CIN2O2的7-氯-6-哌啶-1-基喹啉-5,8-二酮被指定为PT-262。PT-262可以通过稳定F-肌动蛋白和诱导癌细胞中异常肌动蛋白聚合来诱导细胞延长，此外，PT-262具有抗肿瘤活性，可以阻断癌细胞的生存途径，导致癌细胞凋亡，PT-262还可以诱导生长停滞和抑制细胞周期。PT-262稳定了癌细胞的细胞骨架，导致不可逆的细胞延长，降低了细胞周期素B1和磷酸化cdc2蛋白的水平，并抑制了Ras-ERK蛋白的生存信号途径。PT-262还抑制了线粒体膜电位，诱导了癌细胞中caspase-3的激活和凋亡。
• Quinoline quinones and anti-asthmatic use thereof
  申请人：Eli Lilly and Company

  公开号：US04492704A1

  公开（公告）日：1985-01-08

  This invention relates to a class of quinoline quinones, which are useful for the therapy of immediate hypersensitivity reactions, such as asthma, and in treating any condition characterized by excessive release of leukotrienes. This invention also includes a method for treating these conditions, which comprises administering to animals, including humans, an effective dose of the quinoline quinone compounds. A further part of this invention is pharmaceutical formulations containing these pharmacologically-active compounds.

  本发明涉及一类喹啉醌类化合物，可用于治疗即时型超敏反应，如哮喘，并用于治疗任何表现为白三烯过度释放的疾病。本发明还包括一种治疗这些疾病的方法，包括向动物（包括人类）施用喹啉醌类化合物的有效剂量。本发明的另一部分是含有这些药理活性化合物的制药配方。
• Manipulating nitrosative stress to kill pathologic microbes, pathologic helminths and pathologically proliferating cells or to upregulate nitrosative stress defenses
  申请人：——

  公开号：US20030207815A1

  公开（公告）日：2003-11-06

  Mammals are treated for infections or for conditions associated with pathologically proliferating mammalian cell growth (for example certain cancers, restenosis, benign prostatic hypertrophy) by administration of a manipulator of nitrosative stress to selectively kill or reduce the growth of the microbes or helminths causing the infection or of host cells infected with the microbes or of the pathologically proliferating mammalian cells. Novel agents include &agr;-alkyl-S-alkyl-homocysteine sulfoximines wherein the &agr;-alkyl contains 2 to 8 carbon atoms, and the S-alkyl-contains 1 to 10 carbon atoms. In another invention herein, mammals in need of increased nitrosative stress defenses are treated, e.g., humans at risk for a stroke because of having had a transient ischemic attack, are treated. Treatments to increase nitrosative stress defenses include, for example, repeated administrations of low doses of manipulators of nitrosative stress so that the subject treated has increased tolerance to nitrosative stress. In still another invention, mammals are treated for protozoal infections by systemic administration of L-buthionine-S-sulfoximine and agent that increases nitrosative stress.

  哺乳动物被治疗感染或与病理增殖哺乳动物细胞生长相关的情况（例如某些癌症，再狭窄，良性前列腺增生）通过给予一种硝化应激调节剂，以选择性地杀死或减少微生物或蠕虫引起的感染或受微生物感染的宿主细胞或病理增殖的哺乳动物细胞的生长。新型药剂包括α-烷基-S-烷基-同型半胱氨酸亚砜，其中α-烷基含2至8个碳原子，S-烷基含1至10个碳原子。在本发明的另一种方法中，需要增加硝化应激防御的哺乳动物被治疗，例如，由于患有短暂性缺血性发作而处于中风风险的人类被治疗。增加硝化应激防御的治疗包括例如反复给予低剂量的硝化应激调节剂，以使受治疗的对象对硝化应激具有增加的耐受性。在另一种发明中，哺乳动物通过系统给药L-丁硫氧嘧啶和增加硝化应激的药物来治疗原虫感染。