4'-(benzyloxy)-4-methoxy-3'-methyl-2-nitrobiphenyl | 1021685-18-6

• 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'-(benzyloxy)-4-methoxy-3'-methyl-2-nitrobiphenyl
• 英文别名: 4-(4-Methoxy-2-nitrophenyl)-2-methyl-1-phenylmethoxybenzene
• CAS: 1021685-18-6
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: WZSAVRGWIWQJPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-(benzyloxy)-4-methoxy-3'-methyl-2-nitrobiphenyl 在 三苯基膦 作用下， 以 1,3-二氯苯 为溶剂， 反应 48.0h， 以0.22 g的产率得到KED-3-63-1
  参考文献：
  名称：

  Fluorescent Epigenetic Small Molecule Induces Expression of the Tumor Suppressor Ras-Association Domain Family 1A and Inhibits Human Prostate Xenograft

  摘要：

  Epigenetic silencing of Ras-association domain family 1A (RASSF1A) protein in cancer cells results in a disruption of cell cycle control, genetic instability, enhanced cell motility, and apoptotic resistance. Ectopic expression of RASSF1A reverses this tumorigenic phenotype. Thus, small molecules with the ability to restore RASSF1A expression may represent a new class of therapeutic agents. Recently, we designed and synthesized a fluorescent carbazole analogue of mahanine (alkaloid from Murraya koenigii) that restored RASSF1A mRNA expression. Our fluorescent lead compound up-regulated RASSF1A in vitro, potently inhibited human prostate cancer cell proliferation, and fluoresced at a visible wavelength, allowing for the observation of intracellular distribution. The small molecule lead was not acutely toxic up to 550 mg/kg, and dosing at 10 mg/kg reduced human xenograft tumor volume by about 40%.

  DOI：

  10.1021/jm9011615
• 作为产物：
  描述：

  1-(benzyloxy)-4-iodo-2-methylbenzene 、 4-溴-3-硝基苯甲醚 在 palladium diacetate potassium carbonate 作用下， 以 PEG 为溶剂， 以40%的产率得到4'-(benzyloxy)-4-methoxy-3'-methyl-2-nitrobiphenyl
  参考文献：
  名称：

  WO2008/51523

  摘要：

  公开号：

文献信息

• 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。
• CANCER THERAPY
  申请人：Banerjee Partha

  公开号：US20100130579A1

  公开（公告）日：2010-05-27

  The present invention relates to methods of inducing expression of an epigenetically silenced gene, RASSF1A, in cells, particularly human cells, such as cancer cells. It also relates to methods of treating an individual, prophylactically or therapeutically, for cancer in which RASSF1A is epigenetically silenced.

  本发明涉及诱导细胞中表观遗传学沉默基因RASSF1A表达的方法，特别是人类细胞，如癌细胞。它还涉及治疗个体的方法，预防或治疗RASSF1A表观遗传学沉默引起的癌症。
• 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。
• [EN] FLUORESCENT REGULATORS OF RASSF1A EXPRESSION AND HUMAN CANCER CELL PROLIFERATION<br/>[FR] RÉGULATEURS FLUORESCENTS DE L'EXPRESSION DE RASSF1A ET DE LA PROLIFÉRATION DE CELLULES CANCÉREUSES HUMAINES
  申请人：UNIV GEORGETOWN

  公开号：WO2010019271A8

  公开（公告）日：2011-03-31