(1,4-dimethoxy-3-methylnaphthalen-2-yl)acetic acid | 253863-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetic acid
• 英文别名: 1,4-Dimethoxy-3-methyl-2-naphthylacetic acid；MX-7；2-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)acetic acid
• CAS: 253863-53-5
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: OSVWCEJPZZLXLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetic acid 在 N-溴代丁二酰亚胺(NBS) 、 ammonium cerium(IV) nitrate 、 air 、 硫酸 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 水 、 乙腈 为溶剂， 反应 12.5h， 生成 2-isobutylbenzo[g]isoquinoline-3,5,10(2H)-trione
  参考文献：
  名称：

  New synthesis of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones

  摘要：

  Various N-substituted benz[g]isoquinoline-3,5,10(2H)-triones 7 were prepared starting from vitamin K-3 (menadione) 9. The key steps involve substitution of a benzylic bromide by a primary amine and intramolecular condensation across the ester moiety of a (3-bromo-methyl -naphth-2-yl) acetate 8 followed by oxidation with cerium(IV) ammonium nitrate (CAN) and spontaneous dehydrogenation, resulting in the title compounds 7. A selection of the synthesised new compounds was tested in vitro against Mycobacterium tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.052
• 作为产物：
  描述：

  ethyl (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetate 在 盐酸 、 氢氧化钾 、 tin(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetic acid
  参考文献：
  名称：

  Synthesis of Two Naphthoquinone Antibiotics Pentalongin and Psychorubrin

  摘要：

  DOI：

  10.1055/s-1999-3613

文献信息

• Synthesis of 2-methyl-1,4-naphthoquinones with higher gamma-glutamyl carboxylase activity than MK-4 both in vitro and in vivo
  作者：Cees Vermeer、Cynthia van 't Hoofd、Marjo H.J. Knapen、Sofia Xanthoulea

  DOI：10.1016/j.bmcl.2016.11.073

  日期：2017.1

  cells than menaquinone-4 (MK-4, form of vitamin K2). Longer side chain lengths resulted in lower bioactivity. The in vivo vitamin K activity of the C-14 tail derivative was further tested in WKY rats receiving a vitamin K-deficient diet that resulted in a 40% decrease of prothrombin activity. The C-14 tail derivative was able to counteract the effects on vitamin K deficiency induced by the diet and resulted

  维生素K是共有2-甲基-1,4-萘醌环但在3位侧链不同的化合物的总称。我们合成了3-位不同侧链长度的新型2-甲基-1,4-萘醌衍生物。具有C-14和C-16尾巴的衍生物显示出最高的体外生物活性，从而导致MG63细胞中羧化骨钙素的合成比甲萘醌4（MK-4，维生素K2的形式）高2.5到2倍。较长的侧链长度导致较低的生物活性。在体内在接受维生素K缺乏饮食的WKY大鼠中进一步测试了C-14尾部衍生物的维生素K活性，从而导致凝血酶原活性降低了40％。C-14尾部衍生物能够抵消饮食对维生素K缺乏症的影响，并导致凝血酶原活性的完全恢复。与天然形式的维生素K相比，合成维生素K衍生物可能具有更高的生物活性和不同的药理特性，因此更适合用作补充剂或用于临床环境。
• [EN] NOVEL 2-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES AND PRECURSORS THEREOF, HAVING VITAMIN K ACTIVITY<br/>[FR] NOUVEAUX DÉRIVÉS DE 2-MÉTHYL-1,4-NAPHTOQUINONE ET PRÉCURSEURS DE CEUX-CI, AYANT UNE ACTIVITÉ VITAMINE K
  申请人：NATTOPHARMA ASA

  公开号：WO2011098545A1

  公开（公告）日：2011-08-18

  New 2-methyl-1,4-naphthoquinone derivatives with vitamin K activity are provided having the general formula (1): wherein R is a aliphatic group with 12 to 50 carbon atoms. Preferably, R is a straight or branched C12-50 alkylgroup or a straight or branched C12-50 alkenyl group with 1 to 12 unsaturated bonds. Of these, the compound of formula (1) in which R is a straight C14 alkyl group is most preferred. Pharmaceutical and nutraceutical compositions comprising at least one compound of formula (1) or a pharmacologically active precursor there of are also provided.
• New synthesis of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones
  作者：Jan Jacobs、Sven Claessens、Bart Kesteleyn、Kris Huygen、Norbert De Kimpe

  DOI：10.1016/j.tet.2006.12.052

  日期：2007.3

  Various N-substituted benz[g]isoquinoline-3,5,10(2H)-triones 7 were prepared starting from vitamin K-3 (menadione) 9. The key steps involve substitution of a benzylic bromide by a primary amine and intramolecular condensation across the ester moiety of a (3-bromo-methyl -naphth-2-yl) acetate 8 followed by oxidation with cerium(IV) ammonium nitrate (CAN) and spontaneous dehydrogenation, resulting in the title compounds 7. A selection of the synthesised new compounds was tested in vitro against Mycobacterium tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Two Naphthoquinone Antibiotics Pentalongin and Psychorubrin
  作者：Bart Kesteleyn

  DOI：10.1055/s-1999-3613

  日期：1999.11