4-[3,4-Dimethoxy-2-n-propylphenyl]-3-methylbutanoicAcid | 213971-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[3,4-Dimethoxy-2-n-propylphenyl]-3-methylbutanoicAcid
• 英文别名: 3,4-Dimethoxy-I(2)-methyl-2-propylbenzenebutanoic acid；4-(3,4-dimethoxy-2-propylphenyl)-3-methylbutanoic acid
• CAS: 213971-36-9
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: GBYYJKNCLBJQAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  4-[3,4-Dimethoxy-2-n-propylphenyl]-3-methylbutanoicAcid 在 polyphosphoric ester 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到3,4-dihydro-6,7-dimethoxy-3-methyl-5-n-propyl-1(2H)naphthalenone
  参考文献：
  名称：

  Selective Inhibitors of Human Lactate Dehydrogenases and Lactate Dehydrogenase from the Malarial Parasite Plasmodium falciparum

  摘要：

  Derivatives of the sesquiterpene 8-deoxyhemigossylic acid (2,3-dihydroxy-6-methyl-4-(1-methylethyl)-1-naphthoic acid) were synthesized that contained altered alkyl groups in the 4-position and contained alkyl or aralkyl groups in the 7-position. These substituted dihydroxynaphthoic acids are selective inhibitors of human lactate dehydrogenase-H (LDHH) and LDH-M and of lactate dehydrogenase from the malarial parasite Plasmodium falciparum (pLDH). All inhibitors are competitive with the binding of NADH. Selectivity for LDH-H, LDH-M, or pLDH is strongly dependent upon the groups that are in the 4- and 7-positions of the dihydroxynaphthoic acid backbone. Dissociation constants as low as 50 nM were observed, with selectivity as high as 400-fold.

  DOI：

  10.1021/jm980334n
• 作为产物：
  描述：

  1-bromo-3,4-dimethoxy-2-propylbenzene 在 palladium on activated charcoal 氢氧化钾 、 溴乙烷 、 氢气 、 magnesium 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 25.0~60.0 ℃ 、413.69 kPa 条件下， 反应 29.0h， 生成 4-[3,4-Dimethoxy-2-n-propylphenyl]-3-methylbutanoicAcid
  参考文献：
  名称：

  Selective Inhibitors of Human Lactate Dehydrogenases and Lactate Dehydrogenase from the Malarial Parasite Plasmodium falciparum

  摘要：

  Derivatives of the sesquiterpene 8-deoxyhemigossylic acid (2,3-dihydroxy-6-methyl-4-(1-methylethyl)-1-naphthoic acid) were synthesized that contained altered alkyl groups in the 4-position and contained alkyl or aralkyl groups in the 7-position. These substituted dihydroxynaphthoic acids are selective inhibitors of human lactate dehydrogenase-H (LDHH) and LDH-M and of lactate dehydrogenase from the malarial parasite Plasmodium falciparum (pLDH). All inhibitors are competitive with the binding of NADH. Selectivity for LDH-H, LDH-M, or pLDH is strongly dependent upon the groups that are in the 4- and 7-positions of the dihydroxynaphthoic acid backbone. Dissociation constants as low as 50 nM were observed, with selectivity as high as 400-fold.

  DOI：

  10.1021/jm980334n

文献信息

• Hydroxynaphthoic acids and derivatives
  申请人：University Of New Mexico

  公开号：US06124498A1

  公开（公告）日：2000-09-26

  In one embodiment, the present invention provides a compound comprising: ##STR1## wherein A=H or OH X=OH, a halogen, OR, NHR, NR'R" where R, R', and R"=H, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, or C.sub.2-8 alkynyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or heterocyclic, substituted or unsubstituted; and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 =H, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, or C.sub.2-8 alkynyl, cycloalkyl, cyloalkenyl, aryl or heterocyclic, substituted or unsubstituted, wherein R.sub.1 includes at least one methylene spacer through which R.sub.1 is attached to said compound. The present invention also provides methods for making hydroxynaphthoic acids.

  在一种实施例中，本发明提供一种化合物，包括：##STR1## 其中A=H或OH，X=OH，卤素，OR，NHR，NR'R"，其中R，R'和R"=H，C.sub.1-8烷基，C.sub.2-8烯基，或C.sub.2-8炔基，环烷基，环烯基，芳基，芳基烷基或杂环基，取代或未取代；且R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5=H，C.sub.1-8烷基，C.sub.2-8烯基，或C.sub.2-8炔基，环烷基，环烯基，芳基或杂环基，取代或未取代，其中R.sub.1包括至少一个亚甲基间隔，通过该亚甲基间隔与所述化合物相连接。本发明还提供制备羟基萘酸的方法。
• EP0980350A4
  申请人：——

  公开号：EP0980350A4

  公开（公告）日：2003-01-02
• HYDROXYNAPHTHOIC ACIDS AND DERIVATIVES
  申请人：The University of New Mexico

  公开号：EP0980350A2

  公开（公告）日：2000-02-23
• US6124498A
  申请人：——

  公开号：US6124498A

  公开（公告）日：2000-09-26
• [EN] HYDROXYNAPHTHOIC ACIDS AND DERIVATIVES<br/>[FR] ACIDES HYDROXYNAPHTOIQUES ET DERIVES DE CES DERNIERS
  申请人：——

  公开号：WO1998049130A2

  公开（公告）日：1998-11-05

  [EN] In one embodiment, the present invention provides a compound comprising formula (I), wherein A = H or OH, X = OH, a halogen, OR, NHR, NR', R'' where R, R', and R'' = H, C1-8alkyl, C2-8alkenyl, or C2-8alkynyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or heterocyclic, substituted or unsubstituted; and R1,R2,R3,R4,R5 = H, C1-8alkyl, C2-8alkenyl, or C2-8alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclic, substituted or unsubstituted, wherein R1 includes at least one methylene spacer through which R1 is attached to said compound. The present invention also provides methods for making hydroxynaphthoic acids.
  [FR] Dans une forme de réalisation cette invention concerne un composé de formule (I). Dans cette formule, A représente H ou OH; X rep résente OH, un halogène, OR, NHR, NR'R'', où R, R' et R'' représentent H, alkyle C1-8, alcényle C2-8 ou alkynyle C2-8, cycloalkyle, cycloalcényle, aryle, aralkyle ou groupe hétérocyclique, substitué ou non; et R1,R2,R3,R4,R5 représentent H, alkyle C1-8, alcényle C2-8, ou alkynyle C2-8, cycloalkyle, cycloalcényle, aryle, groupe hétérocyclique, substitué ou non substitué, R1 comprenant au moins un espaceur méthylène par lequel R1 est attaché audit composé. Cette invention concerne également des procédés de production d'acides hydroxynaphtoïques.