7-methoxy-3-methyl-9H-carbazol-2-ol | 38826-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-methoxy-3-methyl-9H-carbazol-2-ol
• 英文别名: 2-Hydroxy-7-methoxy-3-methylcarbazole
• CAS: 38826-49-2
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: UINLHXOQEZLAPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-methyl-9H-carbazol-2-ol 在 hexadecafluorophthalocyanine iron(III) 、 溶剂黄146 作用下， 反应 0.5h， 以61%的产率得到2,2′-dihydroxy-7,7′-dimethoxy-3,3′-dimethyl-1,1′-bicarbazole
  参考文献：
  名称：

  铁（III）催化的2-和1-羟基咔唑的氧化偶联反应合成1,1'-和2,2'-联咔唑生物碱

  摘要：

  我们描述了通过2-羟基和1-羟基咔唑的氧化均偶联来合成1,1'-和2,2'-联咔唑。使用催化量的F 16 PcFe的氧化偶合可应用于两组基材。F尽管也16 PCFE通常提供的1,1'- bicarbazoles合成最好的产率，二-叔过氧化丁酯为2,2'-联咔唑提供了更好的结果。在我们的研究中，我们已经完成了双卡巴菌毒素A-C，双糖胺B，2,2'-二羟基-7,7'-二甲氧基-3,3'-二甲基-1,1'-联咔唑，双吡a啉C的首次合成，和双西马嘌呤。铁链烯酮的催化偶合提高了8,8'-二甲烯胺的合成能力，并提供了前所未有的癸酰基产物。1-羟基咔唑的氧化偶合生成了比屈烯醇和第一个总合成的比莫拉佛林B和D.

  DOI：

  10.1002/chem.201704554
• 作为产物：
  描述：

  2-(tert-butyldiphenylsilyloxy)-7-methoxy-3-methyl-9H-carbazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到7-methoxy-3-methyl-9H-carbazol-2-ol
  参考文献：
  名称：

  Total synthesis and neuroprotective effect of O-methylmurrayamine A and 7-methoxymurrayacine

  摘要：

  O-Methylmurrayamine A (7) and 7-methoxymurrayacine (8) are natural products isolated from Murraya koenigii and Murraya siamensis, respectively. In this paper, we report the synthesis of 7 and 8 which are featured in the key step of cyclization to form carbazole intermediate 5 with mild conditions. The structures were confirmed by H-1 NMR, C-13 NMR, and HR-ESI-MS. In addition, compounds 7 and 8 were tested for their neuroprotective effects against H2O2 -induced PC12 cell damage. The results showed that compounds 7 and 8 have neuroprotective effect.

  DOI：

  10.1080/10286020.2017.1327952

文献信息

• Palladium(<scp>ii</scp>)-catalysed total synthesis of naturally occurring pyrano[3,2-<i>a</i>]carbazole and pyrano[2,3-<i>b</i>]carbazole alkaloids
  作者：Ronny Hesse、Anne Jäger、Arndt W. Schmidt、Hans-Joachim Knölker

  DOI：10.1039/c4ob00367e

  日期：——

  Seven naturally occurring pyranocarbazole alkaloids (pyrayafoline A–E, O-methylmurrayamine A and O-methylmahanine) have been obtained by total synthesis using a palladium(II)-catalysed oxidative cyclisation of a diarylamine to an orthogonally diprotected 2,7-dihydroxycarbazole as key step.

  通过使用钯（II）催化的二芳基胺氧化环化成正交双保护的2,7-二羟基咔唑作为关键化合物，通过全合成获得了七种自然存在的吡喃咔唑生物碱（吡ray啉A–E，O-甲基墨胺A和O-甲基麻红碱）步。
• Iron‐Catalyzed Oxidative C−O and C−N Coupling Reactions Using Air as Sole Oxidant**
  作者：Alexander Purtsas、Marco Rosenkranz、Evgenia Dmitrieva、Olga Kataeva、Hans‐Joachim Knölker

  DOI：10.1002/chem.202104292

  日期：2022.4.12

  Iron-catalyzed oxidative carbon−heteroatom bond formations using air as sole oxidant provide a variety of oxygenated and aminated arylamines as well as aminated phenols. The appropriate additive (Brønsted acid, Lewis acid, or base) is crucial for these couplings. The mild oxidative reaction proceeds at room temperature and represents a powerful alternative to traditional carbon−heteroatom couplings

  使用空气作为唯一氧化剂的铁催化氧化碳-杂原子键的形成提供了各种含氧和胺化芳胺以及胺化酚。适当的添加剂（布朗斯台德酸、路易斯酸或碱）对于这些偶联至关重要。温和的氧化反应在室温下进行，是传统碳-杂原子偶联的有力替代方案。
• [EN] SMALL MOLECULE ANDROGEN RECEPTOR INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] PETITES MOLÉCULES INHIBITRICES DU RÉCEPTEUR DES ANDROGÈNES ET PROCÉDÉS D'UTILISATION DE CES DERNIÈRES
  申请人：UNIV GEORGETOWN

  公开号：WO2017023916A1

  公开（公告）日：2017-02-09

  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。
• FLUORESCENT REGULATORS OF RASSF1A EXPRESSION AND HUMAN CANCER CELL PROLIFERATION
  申请人：Brown Milton L.

  公开号：US20110152339A1

  公开（公告）日：2011-06-23

  The invention provides methods for the treatment of cancer in a subject comprising administering a dansyl-carbazole compound.

  本发明提供了一种治疗癌症的方法，包括给予丹磺酰基-咔唑类化合物给受试者。
• Fluorescent regulators of RASSF1A expression and human cancer cell proliferation
  申请人：Georgetown University

  公开号：EP2484666A1

  公开（公告）日：2012-08-08

  The invention provides carbazole compounds, and prodrugs therefor, comprising a heterogroup coupled to an aryl group, wherein the heterogroup is selected from the group consisting of SO2, S=O, C=O, NH, and PO3. The aryl group may be substituted with one or more substituents selected from the group consisting of OH, NH2, NR1R2, NHR1, OCH3, OCHR1R2, OCH2R1, OCR1R2R3, C=O, or S=O, wherein R1, R2, and R3 are alkyl groups, optionally wherein the heterogroup coupled to the aryl group is a dansyl group, and optionally wherein the heterogroup coupled to the aryl group is a fluorescent group. The compounds are useful for the treatment of cancers, especially those with decreased Ras-association domain family 1A (RASSF1A) expression, including prostate cancer. The compounds may reduce DNA methyltransferase activity and/or increase RASSF1A expression. Retention of the compound in a cell is diagnostic for decreased RASSF1A expression, and hence potentially for a cancer cell.

  本发明提供了咔唑化合物及其原药，其包含与芳基偶联的杂基，其中杂基选自由SO2、S=O、C=O、NH和PO3组成的组。芳基可被一个或多个取代基取代，这些取代基选自由 OH、NH2、NR1R2、NHR1、OCH3、OCHR1R2、OCH2R1、OCR1R2R3、C=O 或 S=O 组成的组，其中 R1、R2 和 R3 为烷基，偶联至芳基的杂基可选为丹酰基，偶联至芳基的杂基可选为荧光基。 这些化合物可用于治疗癌症，尤其是 Ras-association domain family 1A (RASSF1A) 表达降低的癌症，包括前列腺癌。化合物可降低 DNA 甲基转移酶活性和/或增加 RASSF1A 的表达。 化合物在细胞中的滞留可诊断出 RASSF1A 表达的降低，从而可能诊断出癌细胞。