2-(cyclohexylmethoxy)benzaldehyde | 1020948-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(cyclohexylmethoxy)benzaldehyde
• CAS: 1020948-32-6
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: XKKZWQDMPXIYSA-UHFFFAOYSA-N

物化性质

• 沸点：
  347.3±15.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(cyclohexylmethoxy)benzaldehyde 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 6.0h， 生成 methyl 4-(cyclohexylmethoxy)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives

  摘要：

  Based on the chemical structure of Pyrroloquinoline quinone (PQQ), a novel class of indole-2-carboxylate derivatives was designed, synthesized and assayed for antiproliferative activity in cancer cells in vitro. The biological results showed that some derivatives exhibited significant antiproliferative activity against HepG2, A549 and MCF7 cells. Notably, the novel compounds, methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate (6e) and methyl 4-isopropoxy-6-methoxy-1H-indole-2-carboxylate (9l) exhibited more potent antiproliferative activity than the reference drugs PQQ and etoposide in vitro, with IC50 values ranging from 3.78 ± 0.58 to 24.08 ± 1.76 μM. Further biological assay showed that both compounds 6e and 9l increased ROS generation dose-dependently, and induced PARP cleavage in A549 cells. Consequently, 6e and 9l appeared as promising anticancer lead compounds for further optimization.

  DOI：

  10.1016/j.ejmech.2014.05.043
• 作为产物：
  描述：

  在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 2-(cyclohexylmethoxy)benzaldehyde
  参考文献：
  名称：

  PRMTI型甲基转移酶抑制活性化合物及其制备与应用

  摘要：

  本发明涉及一种具有PRMT I型甲基转移酶抑制活性的化合物及其制备与应用，所述化合物具有式I所示的结构；本发明的式I化合物对PRMT I型甲基转移酶具有较好的抑制作用，对PRMT II型甲基转移酶抑制作用较弱，并且对正常细胞影响较小，具有更低的毒副作用，I。

  公开号：

  CN113582864A

文献信息

• [EN] N-BENZYL OXAZOLIDINONES AND RELATED HETEROCYCLEIC COMPOUNDS AS POTENTIATORS OF GLUTAMATE RECEPTORS<br/>[FR] N-BENZYL OXAZOLIDINONES ET COMPOSÉS HÉTÉROCYCLIQUES APPARENTÉS COMME POTENTIALISATEURS DE RÉCEPTEURS DU GLUTAMATE
  申请人：PFIZER

  公开号：WO2009004430A1

  公开（公告）日：2009-01-08

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed. The compounds are active as potentiators of glutamate receptors, in particular mGluR2.

  本发明揭示了化合物及其在规范中定义的Formula（I）结构的药学上可接受的盐，相应的药物组合物、治疗方法、合成方法和中间体也被揭示。这些化合物作为谷氨酸受体的增强剂活性，特别是mGluR2。
• HETEROCYCLIC COMPOUNDS
  申请人：Duplantier Allen J.

  公开号：US20090137577A1

  公开（公告）日：2009-05-28

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  本文披露了化合物及其药学上可接受的盐，其中化合物具有规范中定义的I式结构。还披露了相应的药物组合物、治疗方法、合成方法和中间体。
• SUBSTITUTED ALDEHYDE COMPOUNDS AND METHODS FOR THEIR USE IN INCREASING TISSUE OXYGENATION
  申请人：GLOBAL BLOOD THERAPEUTICS, INC.

  公开号：US20160039801A1

  公开（公告）日：2016-02-11

  Provided are cycloalkyl- and cycloalkenyl-substituted benzaldehydes and heteroaldehydes of formula (I) that act as allosteric modulators of hemoglobin, methods and intermediates for their preparation, pharmaceutical compositions containing the modulators, and methods for their use in treating disorders mediated by hemoglobin and disorders that would benefit from increased tissue oxygenation.

  提供的是公式(I)的环烷基和环烯基取代的苯甲醛和杂原子醛，它们作为血红蛋白的别构调节剂，以及它们的制备方法和中间体、含有调节剂的制药组合物，以及用于治疗由血红蛋白介导的疾病和需要增加组织氧合的疾病的方法。
• Tuning the Metabolic Stability of Visual Cycle Modulators through Modification of an RPE65 Recognition Motif
  作者：Marco Bassetto、Jordan Zaluski、Bowen Li、Jianye Zhang、Mohsen Badiee、Philip D. Kiser、Gregory P. Tochtrop

  DOI：10.1021/acs.jmedchem.3c00461

  日期：2023.6.22

  further development including: (1) metabolic deamination of the γ-amino-α-aryl alcohol, which mediates targeted RPE65 inhibition, and (2) unwanted long-lasting RPE65 inhibition. We sought to address these issues by more broadly defining the structure–activity relationships of the RPE65 recognition motif via the synthesis of a family of novel derivatives, which were tested in vitro and in vivo for RPE65

  在眼睛中，全反式视网膜向 11-顺式视网膜的异构化是通过称为视觉周期的代谢途径完成的，该途径对视力至关重要。RPE65 是该通路必需的反式顺式异构酶。Emixusat 是一种类维生素 A 模拟物 RPE65 抑制剂，被开发为治疗性视觉周期调节剂，用于治疗视网膜病变。然而，药代动力学责任限制了其进一步发展，包括：（1） γ-氨基-α-芳醇的代谢脱氨，介导靶向 RPE65 抑制，以及 （2） 不需要的持久 RPE65 抑制。我们试图通过合成一系列新型衍生物来更广泛地定义 RPE65 识别基序的结构-活性关系来解决这些问题，这些衍生物在体外和体内进行了 RPE65 抑制测试。我们鉴定了一种有效的仲胺衍生物，具有脱氨抗性并保留了 RPE65 抑制活性。我们的数据提供了对 emixustat 分子的活性保持修饰的见解，可用于调整其药理特性。
• Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives
  作者：Xing-yue Ji、Si-tu Xue、Yue-chen Zhan、Jia-jia Shen、Lin-tao Wu、Jie Jin、Zhen Wang、Zhuo-rong Li

  DOI：10.1016/j.ejmech.2014.05.043

  日期：2014.8

  Based on the chemical structure of Pyrroloquinoline quinone (PQQ), a novel class of indole-2-carboxylate derivatives was designed, synthesized and assayed for antiproliferative activity in cancer cells in vitro. The biological results showed that some derivatives exhibited significant antiproliferative activity against HepG2, A549 and MCF7 cells. Notably, the novel compounds, methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate (6e) and methyl 4-isopropoxy-6-methoxy-1H-indole-2-carboxylate (9l) exhibited more potent antiproliferative activity than the reference drugs PQQ and etoposide in vitro, with IC50 values ranging from 3.78 ± 0.58 to 24.08 ± 1.76 μM. Further biological assay showed that both compounds 6e and 9l increased ROS generation dose-dependently, and induced PARP cleavage in A549 cells. Consequently, 6e and 9l appeared as promising anticancer lead compounds for further optimization.