2,2-dimethyl-5-(2,4,5-trimethoxybenzylidene)-1,3-dioxane-4,6-dione | 117646-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2-dimethyl-5-(2,4,5-trimethoxybenzylidene)-1,3-dioxane-4,6-dione
• 英文别名: 5-(2,4,5-trimethoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione；2,2-Dimethyl-5-[(2,4,5-trimethoxyphenyl)methylidene]-1,3-dioxane-4,6-dione
• CAS: 117646-11-4
• 化学式: C₁₆H₁₈O₇
• 分子量: 322.315
• InChiKey: JYKTZKPJXFZDMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(2,4,5-trimethoxybenzylidene)-1,3-dioxane-4,6-dione 在 硫酸 作用下， 反应 2.0h， 以87%的产率得到6,7-dimethoxy-2-oxo-2H-chromene-3-carboxylic acid
  参考文献：
  名称：

  Armstrong, Veronica; Soto, Oriana; Valderrama, Jaime A., Synthetic Communications, 1988, vol. 18, # 7, p. 717 - 726

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 2,4,5-三甲氧基苯甲醛 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-dimethyl-5-(2,4,5-trimethoxybenzylidene)-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  2,2-二甲基-1,3-二恶烷-4,6-二酮的甲氧基亚苄基衍生物及其饱和类似物与某些亲核试剂的反应

  摘要：

  实现了2,2-二甲基-1,3-二恶烷-4,6-二酮的甲氧基亚苄基衍生物及其饱和类似物与氢氧化钾在甲醇，氨和水合肼中的反应。制备并表征了适合用作合成基于它们的各种结构的结构嵌段的甲氧基亚苄基-丙二酸的1,2-双（甲氧基亚苄基）肼，酰胺和酰肼。

  DOI：

  10.1007/s10593-011-0690-7

文献信息

• 신경염증질환의 예방 또는 치료용 신규 화합물 및 이를 포함하는 약제학적 조성물
  申请人：AJOU UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION 아주대학교산학협력단(220040257423) BRN ▼124-82-14602

  公开号：KR20210057305A

  公开（公告）日：2021-05-21

  본 발명은 신규한 2,4,5-트리하이드록시페닐 아크릴레이트 유사체 및 이를 유효성분으로 함유하는 신경염증질환의 예방 또는 치료용 조성물에 관한 것으로, 보다 상세하게는 LPS-자극된 BV-2 미세아교세포에서 NO 방출 억제, iNOS 및 COX-2 발현 억제, 전염증성 사이토카인(proinflammatory cytokine) 생성을 억제하는 효과와 미분화세포 또는 분화세포에서 Nurr1 mRNA 발현을 증가를 통하여 도파민 생성에 관여하는 TH (tyrosine hydroxylase)의 발현을 증가시켜 신경세포의 보호 효과도 가지게 되어 항신경염증 보호 활성을 가짐으로써 신경변성질환에 저항성을 나타내며 알츠하이머, 파킨슨병, 뇌졸중 및 다발성 경화증 등의 퇴행성 신경질환의 예방 및 치료용 조성물에 관한 것이다.

  本发明涉及一种新型的2,4,5-三羟基苯丙烯酸酯类似物及其作为有效成分含有的用于预防或治疗神经炎症性疾病的组合物，具体包括在LPS刺激的BV-2微胶质细胞中抑制NO释放、抑制iNOS和COX-2的表达、抑制炎症性细胞因子生成的效果，通过增加未分化或分化细胞中Nurr1 mRNA的表达来参与多巴胺生成，增加酪氨酸羟化酶的表达，从而具有神经细胞的保护作用，表现出抗神经炎症保护活性，对神经变性疾病具有抗抗性，用于预防和治疗退行性神经疾病如阿尔茨海默病、帕金森病、脑卒中和多发性硬化等的组合物。
• Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents
  作者：Harmeet S. Sandhu、Sameer Sapra、Mukesh Gupta、Kunal Nepali、Raju Gautam、Sunil Yadav、Raj Kumar、Sanjay M. Jachak、Manoj Chugh、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2010.06.033

  日期：2010.8

  A series of arylidene analogues of Meldrum's acid were synthesized and evaluated for in vitro antimalarial and antioxidant activities for the first time. The influence of various physico-chemical parameters such as dielectric constant (epsilon), donor number (DN), acceptor number (AN), hydrogen bond donor (HBD), hydrogen bond acceptor (HBA), and solubilizing power of the solvents on Meldrum's acid anion generation and thus on promoting the Knoevenagel condensation of Meldrum's acid with aryl aldehydes has been discussed. Five compounds 9l, 9m, 9n, 9r, and 9s were found to be most active against Plasmodium falciparum with IC(50) values in the range of 9.68-16.11 mu M. Compound 9l exhibited the most potent antimalarial activity (IC(50) 9.68 mu M). The compounds were also found to possess antioxidant activity when tested against DPPH and ABTS free radicals. (C) 2010 Elsevier Ltd. All rights reserved.
• ARMSTRONG, VERONICA;SOTO, ORIANA;VALDERRAMA, JAIME A.;TAPIA, RICARDO, SYNTH. COMMUN., 18,(1988) N 7, 717-725
  作者：ARMSTRONG, VERONICA、SOTO, ORIANA、VALDERRAMA, JAIME A.、TAPIA, RICARDO

  DOI：——

  日期：——
• Armstrong, Veronica; Soto, Oriana; Valderrama, Jaime A., Synthetic Communications, 1988, vol. 18, # 7, p. 717 - 726
  作者：Armstrong, Veronica、Soto, Oriana、Valderrama, Jaime A.、Tapia, Ricardo

  DOI：——

  日期：——
• Reactions of methoxybenzylidene derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione and their saturated analogs with certain nucleophilic reagents
  作者：Z. Tetere、I. Ravina、I. Rijkure、D. Zicane

  DOI：10.1007/s10593-011-0690-7

  日期：2011.3

  The reactions of the methoxybenzylidene derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione and their saturated analogs with potassium hydroxide in methanol, ammonia, and hydrazine hydrate were realized. The 1,2-bis(methoxybenzylidene)hydrazines, amides, and hydrazides of methoxybenzylidene-malonic acid, suitable for use as structural blocks in the synthesis of various structures based on them, were

  实现了2,2-二甲基-1,3-二恶烷-4,6-二酮的甲氧基亚苄基衍生物及其饱和类似物与氢氧化钾在甲醇，氨和水合肼中的反应。制备并表征了适合用作合成基于它们的各种结构的结构嵌段的甲氧基亚苄基-丙二酸的1,2-双（甲氧基亚苄基）肼，酰胺和酰肼。