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(R,S)-4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yldiphenylmethanol

中文名称
——
中文别名
——
英文名称
(R,S)-4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yldiphenylmethanol
英文别名
(4-Chloro-1-methylpyrrolo[3,2-c]pyridin-2-yl)-diphenylmethanol;(4-chloro-1-methylpyrrolo[3,2-c]pyridin-2-yl)-diphenylmethanol
(R,S)-4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yldiphenylmethanol化学式
CAS
——
化学式
C21H17ClN2O
mdl
——
分子量
348.832
InChiKey
BNGYKMZVYSGLGL-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.2
  • 重原子数:
    25
  • 可旋转键数:
    3
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.1
  • 拓扑面积:
    38
  • 氢给体数:
    1
  • 氢受体数:
    2

反应信息

  • 作为产物:
    描述:
    二苯甲酮4-氯-1-甲基吡咯并[3,2-C]吡啶叔丁基锂 作用下, 以 四氢呋喃正庚烷 为溶剂, 反应 2.67h, 以80%的产率得到(R,S)-4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yldiphenylmethanol
    参考文献:
    名称:
    [EN] 5-AZAINDOLE COMPOUNDS WITH ANTICANCER AND ANTIANGIOGENIC ACTIVITIES
    [FR] COMPOSÉS 5-AZAINDOLE AYANT DES ACTIVITÉS ANTI-CANCER ET ANTI-ANGIOGÉNIQUE
    摘要:
    本发明涉及响应以下式(I)的5-氮杂吲哚类化合物的用途,用于药物,更具体地用于预防和/或治疗癌症等疾病和/或疾病,包括癌症;与血管生成相关的疾病;寄生虫病;真菌病;自身免疫性疾病;炎症性疾病;乳头状瘤病毒引起的疣等。该发明还涉及包含该式(I)化合物的药物组合物。至少一种式(I)化合物作为微管药物耐药细胞系细胞周期同步的研究工具的用途也是本发明的一部分。最后,该发明还涉及至少一种式(I)化合物作为除草剂和/或杀藻剂的用途。
    公开号:
    WO2014033597A1
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文献信息

  • [EN] 5-AZAINDOLE COMPOUNDS WITH ANTICANCER AND ANTIANGIOGENIC ACTIVITIES<br/>[FR] COMPOSÉS 5-AZAINDOLE AYANT DES ACTIVITÉS ANTI-CANCER ET ANTI-ANGIOGÉNIQUE
    申请人:CENTRE NAT RECH SCIENT
    公开号:WO2014033597A1
    公开(公告)日:2014-03-06
    The present invention relates to 5-azaindole type compounds responding to the following formula (I): for their use as drugs, and more particularly for the prevention and/or the treatment of diseases and/or disorders chosen amongst cancers; angiogenesis related disorders; parasitic diseases; fungal diseases; autoimmune diseases; inflammatory diseases; warts such as warts caused by papilloma virus. The invention also relates to pharmaceutical compositions comprising such compounds of formula (I). The use of at least one compound of formula (I) as research tool for the cell-cycle synchronization of microtubule drugs resistant cell lines is also part of the invention. Finally, the invention also concerns the use of at least one compound of formula (I) as an herbicide and/or an algaecide.
    本发明涉及响应以下式(I)的5-氮杂吲哚类化合物的用途,用于药物,更具体地用于预防和/或治疗癌症等疾病和/或疾病,包括癌症;与血管生成相关的疾病;寄生虫病;真菌病;自身免疫性疾病;炎症性疾病;乳头状瘤病毒引起的疣等。该发明还涉及包含该式(I)化合物的药物组合物。至少一种式(I)化合物作为微管药物耐药细胞系细胞周期同步的研究工具的用途也是本发明的一部分。最后,该发明还涉及至少一种式(I)化合物作为除草剂和/或杀藻剂的用途。
  • [EN] 5-AZAINDOLE COMPOUNDS WITH ANTICANCER AND ANTIANGIOGENIC ACTIVITIES<br/>[FR] COMPOSÉS DE 5-AZAINDOLE À ACTIVITÉ ANTI-CANCÉREUSE ET ANTI-ANGIOGÉNIQUE
    申请人:CENTRE NAT RECH SCIENT
    公开号:WO2014033497A1
    公开(公告)日:2014-03-06
    The present invention relates to 5-azaindole type compounds responding to the following formula (I): for their use as drugs, and more particularly for the prevention and/or the treatment of diseases and/or disorders chosen amongst cancers; angiogenesis related disorders; parasitic diseases; fungal diseases; autoimmune diseases; inflammatory diseases; warts such as warts caused by papilloma virus. The invention also relates to pharmaceutical compositions comprising such compounds of formula (I). The use of at least one compound of formula (I) as research tool for the cell-cycle synchronization of microtubule drugs resistant cell lines is also part of the invention. Finally, the invention also concerns the use of at least one compound of formula (I) as an herbicide and/or an algaecide.
    本发明涉及响应以下公式(I)的5-氮杂吲哚类化合物,用于作为药物,特别是用于预防和/或治疗癌症;血管生成相关疾病;寄生虫病;真菌病;自身免疫疾病;炎症性疾病;以及由乳头瘤病毒引起的疣等疾病和/或紊乱。本发明还涉及包含该公式(I)的化合物的制药组合物。使用至少一种公式(I)化合物作为细胞周期同步微管薯莨抗药性细胞系的研究工具也是本发明的一部分。最后,本发明还涉及使用至少一种公式(I)化合物作为除草剂和/或杀藻剂。
  • Azaindole derivatives are inhibitors of microtubule dynamics, with anti-cancer and anti-angiogenic activities
    作者:Renaud Prudent、Émilie Vassal-Stermann、Chi-Hung Nguyen、Marjorie Mollaret、Jean Viallet、Agnès Desroches-Castan、Anne Martinez、Caroline Barette、Catherine Pillet、Glaucio Valdameri、Emmanuelle Soleilhac、Attilio Di Pietro、Jean-Jacques Feige、Marc Billaud、Jean-Claude Florent、Laurence Lafanechère
    DOI:10.1111/j.1476-5381.2012.02230.x
    日期:2013.2
    Background and PurposeDrugs targeting microtubules are commonly used for cancer treatment. However, the potency of microtubule inhibitors used clinically is limited by the emergence of resistance. We thus designed a strategy to find new cell‐permeable microtubule‐targeting agents.Experimental ApproachUsing a cell‐based assay designed to probe for microtubule polymerization status, we screened a chemical library and identified two azaindole derivatives, CM01 and CM02, as cell‐permeable microtubule‐depolymerizing agents. The mechanism of the anti‐tumour effects of these two compounds was further investigated both in vivo and in vitro.Key ResultsCM01 and CM02 induced G2/M cell cycle arrest and exerted potent cytostatic effects on several cancer cell lines including multidrug‐resistant (MDR) cell lines. In vitro experiments revealed that the azaindole derivatives inhibited tubulin polymerization and competed with colchicines for this effect, strongly indicating that tubulin is the cellular target of these azaindole derivatives. In vivo experiments, using a chicken chorioallantoic xenograft tumour assay, established that these compounds exert a potent anti‐tumour effect. Furthermore, an assay probing the growth of vessels out of endothelial cell spheroids showed that CM01 and CM02 exert anti‐angiogenic activities.Conclusions and ImplicationsCM01 and CM02 are reversible microtubule‐depolymerizing agents that exert potent cytostatic effects on human cancer cells of diverse origins, including MDR cells. They were also shown to inhibit angiogenesis and tumour growth in chorioallantoic breast cancer xenografts. Hence, these azaindole derivatives are attractive candidates for further preclinical investigations.
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