2-benzyl-1,2,3,4-tetrahydro-10H-chromeno[3,2-c]pyridin-10-one | 58043-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-benzyl-1,2,3,4-tetrahydro-10H-chromeno[3,2-c]pyridin-10-one
• 英文别名: 2-Benzyl-1,2,3,4-tetrahydro-10H-<1>benzopyrano<3,2-c>pyridin-10-on；2-benzyl-1,2,3,4-tetrahydro-chromeno[3,2-c]pyridin-10-one；2-Benzyl-3,4-dihydro-1H-chromeno[3,2-c]pyridin-10(2H)-one；2-benzyl-3,4-dihydro-1H-chromeno[3,2-c]pyridin-10-one
• CAS: 58043-61-1
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: MBCDTAMAJUIOEG-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  445.1±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-1,2,3,4-tetrahydro-10H-chromeno[3,2-c]pyridin-10-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0~40.0 ℃ 、303.99 kPa 条件下， 反应 0.25h， 生成 2-(phenylsulfonyl)-1,2,3,4-tetrahydro-10H-chromeno[3,2-c]pyridin-10-one
  参考文献：
  名称：

  Scouting around 1,2,3,4‐Tetrahydrochromeno[3,2‐ c ]pyridin‐10‐ones for Single‐ and Multitarget Ligands Directed towards Relevant Alzheimer's Targets

  摘要：

  AbstractA number of 1,2,3,4‐tetrahydrochromeno[3,2‐c]pyridin‐10‐one derivatives have been synthesized and screened against different targets involved in the onset and progression of Alzheimer's disease (AD), such as acetyl‐ and butyrylcholinesterase (AChE and BChE), monoamine oxidases A and B (MAO A and B), aggregation of β‐amyloid (Aβ) and reactive oxygen species (ROS) production. Derivatives 1 c, 3 b, 4 and 5 a showed multifaceted profiles of promising anti‐AD features and returned well‐balanced multitargeting inhibitory activities. Moreover, compound 1 f, a potent and selective human MAO B inhibitor (IC50=0.89 μM), proved to be a safe neuroprotectant in a human neuroblastoma cell line (SH‐SY5Y) by improving viability impaired by Aβ1–42 and pro‐oxidant insult. Furthermore, structure–activity relationships (SARs) and docking models were derived in order to assist further hit‐to‐lead optimization stage.

  DOI：

  10.1002/cmdc.202000468
• 作为产物：
  描述：

  水杨醛 、 4-(1-苄基-3,6-二氢-2H-吡啶-4-基)吗啉 生成 2-benzyl-1,2,3,4-tetrahydro-10H-chromeno[3,2-c]pyridin-10-one
  参考文献：
  名称：

  Sliwa,H.; Cordonnier,G., Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 169 - 170

  摘要：

  DOI：

文献信息

• Synthesis, molecular docking, and biological activity of 2-vinyl chromones: Toward selective butyrylcholinesterase inhibitors for potential Alzheimer's disease therapeutics
  作者：Galina F. Makhaeva、Natalia P. Boltneva、Sofya V. Lushchekina、Elena V. Rudakova、Olga G. Serebryakova、Larisa N. Kulikova、Andrei A. Beloglazkin、Roman S. Borisov、Rudy J. Richardson

  DOI：10.1016/j.bmc.2018.08.010

  日期：2018.9

  The inhibitory activity of these chromone derivatives against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and carboxylesterase (CaE) was investigated using the methods of enzyme kinetics and molecular docking. Antioxidant (antiradical) activity of the compounds was assessed in the ABTS assay. The results demonstrated that a subset of the studied chromone derivatives selectively inhibit

  我们研究了一系列取代的chromeno [3,2- c]吡啶，包括我们小组先前合成的化合物和此处报道了其合成的新化合物。将它们的四氢吡啶环在活化炔烃的作用下进行串联转化，生成2-乙烯基取代的色酮，用于制备生物活性色酮系统的含氮衍生物。使用酶动力学和分子对接的方法研究了这些色酮衍生物对乙酰胆碱酯酶（AChE），丁酰胆碱酯酶（BChE）和羧酸酯酶（CaE）的抑制活性。在ABTS分析中评估了化合物的抗氧化（抗自由基）活性。结果表明，研究的色酮衍生物的一个子集选择性抑制BChE，但不表现出抗自由基活性。此外，
• In-vitro and in-silico studies of annelated 1,4,7,8-tetrahydroazocine ester derivatives as nanomolar selective inhibitors of human butyrylcholinesterase
  作者：Modesto de Candia、Alexander A. Titov、Antonio Viayna、Larisa N. Kulikova、Rosa Purgatorio、Brigida Piergiovanni、Mauro Niso、Marco Catto、Leonid G. Voskressensky、F. Javier Luque、Cosimo D. Altomare

  DOI：10.1016/j.cbi.2023.110741

  日期：2023.12

  Based on previous finding showing 2,3,6,11-tetrahydro-1H-azocino[4,5-b]indole as suitable scaffold of novel inhibitors of acetylcholinesterase (AChE), a main target of drugs for the treatment of Alzheimer's disease and related dementias, herein we investigated diverse newly and previously synthesized β-enamino esters (and ketones) derivatives of 1,4,7,8-tetrahydroazocines (and some azonines) fused

  基于先前的研究结果显示 2,3,6,11-四氢-1H-偶氮并[4,5-b]吲哚是乙酰胆碱酯酶 （AChE） 新型抑制剂的合适支架，乙酰胆碱酯酶 （AChE） 是治疗阿尔茨海默病和相关痴呆症的药物的主要靶点，在此β我们研究了 1,4,7,8-四氢偶氮嘧（和一些偶氮）与苯、1H-吲哚、 4H-铬-4-酮和嘧啶-4（3H）-酮。通过四氢吡啶和氮杂平与活化炔烃的多米诺反应制备的 20 种多样化退火的 8 至 9 元氮杂杂环衍生物，测定了对 AChE 和丁酰胆碱酯酶 （BChE） 的抑制活性。作为主要结果，化合物 7c 是四氢嘧啶 [4,5-d] 氮唑嘧啶的烷基氨基衍生物，被发现是一种高效的 BChE 选择性抑制剂，它显示出对人 BChE 的非竞争性/混合型抑制机制，具有个位数纳摩尔抑制常数 （Ki = 7.8 ± 0.2 nM）。7c 的 4 个数量级的 BChE 选择性清楚地反映了亲脂性在与 BChE
• HAKAMYPA, KODZI;OTAKI, XARUO;XORI, XEHJDZI
  作者：HAKAMYPA, KODZI、OTAKI, XARUO、XORI, XEHJDZI

  DOI：——

  日期：——
• Sliwa,H.; Cordonnier,G., Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 169 - 170
  作者：Sliwa,H.、Cordonnier,G.

  DOI：——

  日期：——
• Scouting around 1,2,3,4‐Tetrahydrochromeno[3,2‐ <i>c</i> ]pyridin‐10‐ones for Single‐ and Multitarget Ligands Directed towards Relevant Alzheimer's Targets
  作者：Rosa Purgatorio、Larisa N. Kulikova、Leonardo Pisani、Marco Catto、Modesto Candia、Antonio Carrieri、Saverio Cellamare、Annalisa De Palma、Andrey A. Beloglazkin、Ghulam Reza Raesi、Leonid G. Voskressensky、Cosimo D. Altomare

  DOI：10.1002/cmdc.202000468

  日期：2020.10.19

  AbstractA number of 1,2,3,4‐tetrahydrochromeno[3,2‐c]pyridin‐10‐one derivatives have been synthesized and screened against different targets involved in the onset and progression of Alzheimer's disease (AD), such as acetyl‐ and butyrylcholinesterase (AChE and BChE), monoamine oxidases A and B (MAO A and B), aggregation of β‐amyloid (Aβ) and reactive oxygen species (ROS) production. Derivatives 1 c, 3 b, 4 and 5 a showed multifaceted profiles of promising anti‐AD features and returned well‐balanced multitargeting inhibitory activities. Moreover, compound 1 f, a potent and selective human MAO B inhibitor (IC50=0.89 μM), proved to be a safe neuroprotectant in a human neuroblastoma cell line (SH‐SY5Y) by improving viability impaired by Aβ1–42 and pro‐oxidant insult. Furthermore, structure–activity relationships (SARs) and docking models were derived in order to assist further hit‐to‐lead optimization stage.