1-(1-methoxy-4-(2-propenyloxy)-2-naphthyl)ethan-1-one | 114661-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-methoxy-4-(2-propenyloxy)-2-naphthyl)ethan-1-one
• 英文别名: 3-acetyl-1-allyloxy-4-methoxynaphthalene；2-acetyl-4-allyloxy-1-methoxynaphthalene；Ethanone, 1-[1-methoxy-4-(2-propenyloxy)-2-naphthalenyl]-；1-(1-methoxy-4-prop-2-enoxynaphthalen-2-yl)ethanone
• CAS: 114661-95-9
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: KZBUYQGRZMBMDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-methoxy-4-(2-propenyloxy)-2-naphthyl)ethan-1-one 反应 7.0h， 生成 3-acetyl-2-allyl-4-methoxy-1-naphthol
  参考文献：
  名称：

  萘并吡喃及其 C4 醇通过使用叔丁醇钾在二甲基甲酰胺中的环化取代萘。一般性和立体化学，包括构象，效果

  摘要：

  2-烯丙基-3-(1'-羟乙基)-1,4-二甲氧基萘1的高产立体选择性环化得到反式3,4-二氢-5,10-二甲氧基-1,3-的一般性二甲基萘并[2,3-c]吡喃 2 通过用乙基取代基取代底物中的每个甲氧基并将它们置于与最初报道的相同的环化反应条件下进行研究。对于在氮气下与叔丁醇钾在二甲基甲酰胺中的较短反应时间，衍生的 1-乙基-、4-乙基-和 1,4-二乙基萘全部环化为反式-1,3-二甲基化合物，而较长时间产率增加相应的顺式异构体的比例。在空气中，差向异构 C4 醇 rel-(1R,3R,4S)-3,4-dihydro-5-ethyl-4-hydroxy-10-methoxy-1,3-dimethylnaphtho[2,3-c]pyran 50 和它的 rel-(1R,3R,

  DOI：

  10.1071/ch07301
• 作为产物：
  描述：

  1-乙酰氧基-3-乙酰基-4-甲氧基萘 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.17h， 生成 1-(1-methoxy-4-(2-propenyloxy)-2-naphthyl)ethan-1-one
  参考文献：
  名称：

  Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S., Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 859 - 864

  摘要：

  DOI：

文献信息

• Identification of a potent NAFLD drug candidate for controlling T2DM-mediated inflammation and secondary damage in vitro and in vivo
  作者：Md Samsuzzaman、Jae Hyuk Lee、Hyejin Moon、Jisue Lee、Heaji Lee、Yunsook Lim、Myoung Gyu Park、Hakwon Kim、Sun Yeou Kim

  DOI：10.3389/fphar.2022.943879

  日期：——

  Accumulation of glucose/sugar results in the formation of reactive di-carbonyl compounds such as MGO and GO that interact with several amino acids and proteins to form toxic advanced glycation end products (AGEs). Induction of AGEs breakdown can control symptoms and severity in T2DM and other related complications like NAFLD where AGEs are the key players. Therefore, an AGE cross-link breaker has been suggested for preventing the onset/progression of NAFLD. In this study, we reported novel synthetic naphthalene-2-acyl thiazolium derivatives (KHAGs). Among synthesized KHAG derivatives, we observed that a novel KHAG-04, a 1,4-dimethoxynaphthalen-2-acyl thiazolium salt which is an analog of alagebrium, dramatically cleaves MGO/GO-AGE cross-links, and it also inhibited inflammation by lowering the level of nitric oxide production and IL-1β and TNF-α secretion in LPS and/or MGO-AGE–activated macrophage. Moreover, it also reduced FFA and MGO-AGE–induced lipogenesis in Hep-G2 cells. In mice, KHAG-04 significantly reduced the level of glyoxal in the liver, which was induced by DMC. Furthermore, KHAG-04 treatment significantly reduced blood glucose levels, lipid accumulation, and inflammation in the NAFLD/T2DM animal model. Novel KHAG-04–mediated induction of AGEs breakdown could be the possible reason for its anti-inflammatory, antihyperglycemic, and anti-lipidemic effects in cells and NAFLD in the T2DM animal model, respectively. Further research might explore the pharmacological efficacy and usefulness and consider the ability of this compound in the treatment strategy against various models of NAFLD in T2DM where MGO/GO-AGEs play a key role in the pathogenesis.

  葡萄糖/糖的积累会导致反应性双酮类化合物的形成，如MGO和GO，它们与几种氨基酸和蛋白质相互作用，形成有毒的高级糖基化终产物（AGEs）。诱导AGEs分解可以控制T2DM和其他相关并发症的症状和严重程度，例如AGEs是关键因素的NAFLD。因此，建议使用AGE交联断裂剂来预防NAFLD的发生/进展。在本研究中，我们报道了新型合成的萘-2-酰噻唑衍生物（KHAGs）。在合成的KHAG衍生物中，我们发现一种新型KHAG-04，一种1,4-二甲氧基萘-2-酰噻唑盐，它是alagebrium的类似物，能够显著断裂MGO/GO-AGE交联，并通过降低LPS和/或MGO-AGE激活的巨噬细胞中一氧化氮产生和IL-1β和TNF-α分泌的水平来抑制炎症。此外，它还减少了FFA和MGO-AGE诱导的Hep-G2细胞的脂肪生成。在小鼠中，KHAG-04显著降低了由DMC诱导的肝脏中甘氧醛的水平。此外，KHAG-04治疗显著降低了NAFLD/T2DM动物模型中的血糖水平、脂质积累和炎症。新型KHAG-04介导的AGEs分解诱导可能是其在细胞和T2DM动物模型中抗炎、抗高血糖和抗脂质效应的可能原因。进一步的研究可能会探索该化合物在各种NAFLD模型中的药理功效和有用性，并考虑其在治疗策略中的能力，其中MGO/GO-AGEs在病理发生中起关键作用。
• KRAUS, GEORGE A.;LIRAS, SPIROS;MAN, TIM ON;MOLINA, MARIA TERESA, J. ORG. CHEM., 54,(1989) N3, C. 3137-3139
  作者：KRAUS, GEORGE A.、LIRAS, SPIROS、MAN, TIM ON、MOLINA, MARIA TERESA

  DOI：——

  日期：——
• Synthesis of 4,11-dideoxydaunomycinone by a Claisen/Diels-Alder sequence
  作者：George A. Kraus、Spiros Liras、Tim On Man、Maria Teresa Molina

  DOI：10.1021/jo00274a033

  日期：1989.6
• [EN] NOVEL THIAZOLE DERIVATIVE AND USE THEREOF<br/>[FR] NOUVEAU DÉRIVÉ THIAZOLE ET SON UTILISATION<br/>[KO] 신규한 티아졸 유도체 및 이의 용도
  申请人：UNIV GACHON IND ACAD COOP FOUND

  公开号：WO2021125905A1

  公开（公告）日：2021-06-24

  본 발명은 신규한 티아졸계 화합물 및 이의 용도에 관한 것이다. 본 발명의 신규한 티아졸계 화합물은 최종당화산물(Advanced glycation and product; AGEs)의 생성을 억제하고, 생성된 최종당화산물을 분해하므로, 최종당화산물 관련 질병의 예방 또는 치료에 유용하게 사용될 수 있다.
• Naphthopyrans and their C4 Alcohols by Cyclization of Substituted Naphthalenes using Potassium t-Butoxide in Dimethylformamide. Generality and Stereochemical, including Conformational, Effects
  作者：Robin G. F. Giles、Ivan R. Green、Wendell P. Swigelaar、C. Peter Taylor

  DOI：10.1071/ch07301

  日期：——

  methoxy groups in the substrate by an ethyl substituent and subjecting these to cyclization reaction conditions identical to those originally reported. For shorter reaction times with potassium tert-butoxide in dimethylformamide under nitrogen, the derived 1-ethyl-, 4-ethyl-, and 1,4-diethylnaphthalenes all cyclize to the trans-1,3-dimethyl compounds, whereas longer times yield increasing proportions of

  2-烯丙基-3-(1'-羟乙基)-1,4-二甲氧基萘1的高产立体选择性环化得到反式3,4-二氢-5,10-二甲氧基-1,3-的一般性二甲基萘并[2,3-c]吡喃 2 通过用乙基取代基取代底物中的每个甲氧基并将它们置于与最初报道的相同的环化反应条件下进行研究。对于在氮气下与叔丁醇钾在二甲基甲酰胺中的较短反应时间，衍生的 1-乙基-、4-乙基-和 1,4-二乙基萘全部环化为反式-1,3-二甲基化合物，而较长时间产率增加相应的顺式异构体的比例。在空气中，差向异构 C4 醇 rel-(1R,3R,4S)-3,4-dihydro-5-ethyl-4-hydroxy-10-methoxy-1,3-dimethylnaphtho[2,3-c]pyran 50 和它的 rel-(1R,3R,