4'-methoxy-3-methyl-2'-nitro-[1,1'-biphenyl]-4-ol | 1620094-46-3

• 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'-methoxy-3-methyl-2'-nitro-[1,1'-biphenyl]-4-ol
• 英文别名: 4′-methoxy-3-methyl-2′-nitrobiphenyl-4-ol；4’-methoxy-3-methyl-2’-nitrobiphenyl-4-ol；4-(4-Methoxy-2-nitrophenyl)-2-methylphenol
• CAS: 1620094-46-3
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: BKZDPJANEGTWLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-methoxy-3-methyl-2'-nitro-[1,1'-biphenyl]-4-ol 在 三溴化硼 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 邻二氯苯 为溶剂， 反应 17.0h， 生成 1-methyl-9H-carbazole-2,7-diyl Bis(5-(dimethylamino)-naphthalene-1-sulfonate)
  参考文献：
  名称：

  Novel Carbazole Inhibits Phospho-STAT3 through Induction of Protein–Tyrosine Phosphatase PTPN6

  摘要：

  The aberrant activation of STAT3 occurs in many human cancers and promotes tumor progression. Phosphorylation of a tyrosine at amino acid Y705 is essential for the function of STAT3. Synthesized carbazole derived with fluorophore compound 12 was discovered to target STAT3 phosphorylation. Compound 12 was found to inhibit STAT3-mediated transcription as well as to reduce IL-6 induced STAT3 phosphorylation in cancer cell lines expressing both elevated and low levels of phospho-STAT3 (Y705). Compound 12 potently induced apoptosis in a broad number of TNBC cancer cell lines in vitro and was effective at inhibiting the in vivo growth of human TNBC xenograft tumors (SUM149) without any observed toxicity. Compound 12 also effectively inhibited the growth of human lung tumor xenografts (A549) harboring aberrantly active STAT3. In vitro and in vivo studies showed that the inhibitory effects of 12 on phospho-STAT3 were through up-regulation of the protein-tyrosine phosphatase PTPN6. Our present studies strongly support the continued preclinical evaluation of compound 12 as a potential chemotherapeutic agent for TNBC and cancers with constitutive STAT3 signaling.

  DOI：

  10.1021/jm4018042
• 作为产物：
  描述：

  2-甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)苯酚 、 4-碘基-3-硝基苯甲醚 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.0h， 以87%的产率得到4'-methoxy-3-methyl-2'-nitro-[1,1'-biphenyl]-4-ol
  参考文献：
  名称：

  [EN] SMALL MOLECULE ANDROGEN RECEPTOR INHIBITORS AND METHODS OF USE THEREOF
  [FR] PETITES MOLÉCULES INHIBITRICES DU RÉCEPTEUR DES ANDROGÈNES ET PROCÉDÉS D'UTILISATION DE CES DERNIÈRES

  摘要：

  本文提供了用作雄激素受体抑制剂的小分子咔唑化合物。本文还提供了使用咔唑化合物治疗前列腺癌的方法，包括去势抵抗性前列腺癌和恩扎鲁胺抵抗性前列腺癌的方法。该方法包括向受试者给予本文所述的化合物或组合物的有效量。

  公开号：

  WO2017023916A1

文献信息

• Chemoselective arylation of phenols with bromo-nitroarenes: synthesis of nitro-biaryl-ols and their conversion into benzofurans and carbazoles
  作者：Amit Kumar、Abhimanyu Yadav、Ajay Verma、Sadhan Jana、Moh. Sattar、Shailesh Kumar、Ch. Durga Prasad、Sangit Kumar

  DOI：10.1039/c4cc03090g

  日期：——

  A series of substituted phenols were chemoselectively arylated with bromo-nitroarenes using KO^tBu at room temperature via an S_NAr pathway.

  一系列取代酚在室温下使用KO^tBu与溴化硝基芳烃进行化学选择性芳基化，通过S_NAr途径。
• Small molecule androgen receptor inhibitors and methods of use thereof
  申请人：GEORGETOWN UNIVERSITY

  公开号：US10173978B2

  公开（公告）日：2019-01-08

  Small molecule carbazole compounds for use as androgen receptor inhibitors are provided herein. Also provided herein are methods for using the carbazole compounds in treating prostate cancer, including castration-resistant prostate cancer and enzalutamide-resistant prostate cancer. The methods include administering to a subject an effective amount of a compound or composition as described herein.

  本文提供了用作雄激素受体抑制剂的小分子咔唑化合物。本文还提供了使用咔唑化合物治疗前列腺癌（包括阉割抗性前列腺癌和恩扎鲁胺抗性前列腺癌）的方法。这些方法包括向受试者施用有效量的本文所述化合物或组合物。
• SMALL MOLECULE ANDROGEN RECEPTOR INHIBITORS AND METHODS OF USE THEREOF
  申请人：GEORGETOWN UNIVERSITY

  公开号：US20180215712A1

  公开（公告）日：2018-08-02

  Small molecule carbazole compounds for use as androgen receptor inhibitors are provided herein. Also provided herein are methods for using the carbazole compounds in treating prostate cancer, including castration-resistant prostate cancer and enzalutamide-resistant prostate cancer. The methods include administering to a subject an effective amount of a compound or composition as described herein.