9-chloro-2,7-dimethylacridine | 171108-49-9

• 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
• 英文名称: 9-chloro-2,7-dimethylacridine
• 英文别名: 9-Chlor-2,7-dimethyl-acridin
• CAS: 171108-49-9
• 化学式: C₁₅H₁₂ClN
• 分子量: 241.72
• InChiKey: CQDPSHYTDCHMJM-UHFFFAOYSA-N

物化性质

• 沸点：
  407.6±25.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,7-二氨基庚烷 、 9-chloro-2,7-dimethylacridine 以 苯酚 为溶剂， 反应 8.0h， 以52%的产率得到N1,N7-bis(2,7-dimethylacridin-9-yl)heptane-1,7-diamine
  参考文献：
  名称：

  Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression

  摘要：

  The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.

  DOI：

  10.1021/acs.jmedchem.9b01917
• 作为产物：
  描述：

  2,7-dimethylacridin-9(10H)-one 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 9-chloro-2,7-dimethylacridine
  参考文献：
  名称：

  Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression

  摘要：

  The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.

  DOI：

  10.1021/acs.jmedchem.9b01917

文献信息

• DE632224
  申请人：——

  公开号：——

  公开（公告）日：——
• US5229395A
  申请人：——

  公开号：US5229395A

  公开（公告）日：1993-07-20
• [EN] POTENTIAL ANTICANCER AGENTS DERIVED FROM ACRIDINE
  申请人：SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH

  公开号：WO1991005770A1

  公开（公告）日：1991-05-02

  (EN) The compounds of the subject invention can be represented by formula (I), wherein each of R1, R2, R3, R4 are the same or different and are hydrogen (H), or a lower alkyl group of from about 1-4 carbon atoms, or a lower alkoxy group of from about 1-4 carbon atoms. R is a substituted aniline ($g(a)), wherein one of R5, R6, R7 is an alkanol having the formula -(CH2)nOH, n = 1-4, or its carbamate ester having the formula -(CH2)nOCONR'R'', n = 1-4, and wherein R' and R'' are the same or different lower alkyl groups of from about 1 to 4 carbon atoms, one of R' and R'' may be hydrogen (H), and the remaining groups are hydrogen. Additionally, the subject invention provides methods for synthesizing the above-identified compounds, physiologically acceptable compositions containing these compounds and methods for using these compounds to inhibit the growth of tumor cells.(FR) Les composés décrits peuvent être représentés par la formule (I), où: R1, R2, R3, R4 sont chacun identiques ou différents et représentent l'hydrogène (H) ou un groupe alkyle inférieur d'environ 1 à 4 atomes de carbone ou un groupe alkoxy inférieur d'environ 1 à 4 atomes de carbone; R représente une aniline substituée représentée par la formule ($g(a)), où l'un des éléments R5, R6, R7 représente un alkanol de formule -(CH2)nOH, et n est égal à un nombre compris entre 1 et 4, ou son ester de carbamate de formule -(CH2)nOCONR'R'', et n est égal à un nombre compris entre 1 et 4, et où R'et R'' représentent des groupes alkyle inférieurs identiques ou différents d'environ 1 à 4 atomes de carbone, l'un des éléments R' et R'' pouvant représentés l'hydrogène (H) et les groupes restants représentant l'hydrogène. L'invention se rapporte en outre à des procédés de synthèse de ces composés, à des compositions physiologiquement acceptables contenant ces composés et à des procédés d'utilisation de ces composés en vue d'inhiber la croissance de cellules tumorales.
• Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene <i>c-myc</i> Expression
  作者：Guotao Kuang、Meiling Zhang、Shuangshuang Kang、Dexuan Hu、Xiaoya Li、Zuzhuang Wei、Xue Gong、Lin-Kun An、Zhi-Shu Huang、Bing Shu、Ding Li

  DOI：10.1021/acs.jmedchem.9b01917

  日期：2020.9.10

  The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.