7-(1-naphthyl)heptanoic acid | 109397-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-(1-naphthyl)heptanoic acid
• 英文别名: 7-[1]naphthyl-heptanoic acid；7-[1]Naphthyl-heptansaeure；7-(Naphthalen-1-yl)heptanoic acid；7-naphthalen-1-ylheptanoic acid
• CAS: 109397-88-8
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: OTYCUXCZGNDFQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(1-naphthyl)heptanoic acid 在 草酰氯 作用下， 生成 1-oxo-1-[5-(2-pyridyl)oxazol-2-yl]-7-(1-naphthyl)heptane
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r
• 作为产物：
  描述：

  (5-羧基戊基)三苯基溴化磷 在 palladium on activated charcoal potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 7-(1-naphthyl)heptanoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r

文献信息

• Mittlere ringe-XIII
  作者：R. Huisgen、U. Rietz

  DOI：10.1016/0040-4020(58)88047-3

  日期：1958.5

  The intramolecular Friedel-Crafts cyclisation of ω-arylalkanoic acids, which is in the benzene series a valuable synthetic route to bicyclic ketones with medium-sized and large rings, has been investigated with ω-(1-naphthyl)alkanoyl chlorides. The lower members, including naphthyl-caproic acid, close the ring at position 2 to form IV. The higher homologous acids show a preference for annellation at

  ω-芳基链烷酸的分子内Friedel-Crafts环化是苯系列中具有中型和大环的双环酮的有价值的合成途径，已用ω-（1-萘基）链烷酰氯进行了研究。包括萘基-己酸的低级成员在位置2处闭合环以形成IV。较高的同源酸显示优先选择7位的壬基化，从而提供了一种新型的异核萘环酮（VII）。在ω-（1-萘基）癸酸环化过程中，1,4环的闭合与1,7类型竞争。
• Methods to increase plasma HDL cholesterol levels and improve HDL functionality with probucol monoesters
  申请人：——

  公开号：US20030064967A1

  公开（公告）日：2003-04-03

  It has been discovered that certain selected probucol monoesters, and their pharmaceutically acceptable salts or prodrugs, are useful for increasing circulating HDL cholesterol. These compounds may also improve HDL functionality by (a) increasing clearance of cholesteryl esters, (b) increasing HDL-particle affinity for hepatic cell surface receptors or (c) increasing the half life of apoAI-HDL.

  已经发现某些选择的普布考醇单酯以及它们的药用盐或前药对增加循环高密度脂蛋白胆固醇是有用的。这些化合物还可以通过（a）增加酯化胆固醇的清除、（b）增加高密度脂蛋白颗粒与肝细胞表面受体的亲和力或（c）增加apoAI-HDL的半衰期来改善高密度脂蛋白的功能。
• [EN] PROCESS FOR THE PREPARATION OF 1,2,6,7,8,8A-HEXAHYDRO-BETA,DELTA,6-TRIHYDROXY-2-METHYL-8-[(2S)-2-METHYL-1-OXOBUTOXY]-, (BETA R,DELTA R,1S,2S,6S,8S,8AR)-1-NAPHTHALENEHEPTANOIC ACID, SODIUM SALT.<br/>[FR] PROCEDE PERMETTANT LA PREPARATION DE SEL SODIQUE D'ACIDE 1,2,6,7,8,8A-HEXAHYDRO-BETA, DELTA, 6-TRIHYDROXY-2-METHYL-8-[(2S)-2-METHYL-1-OXOBUTOXY]-, (BETA R, DELTA R,1S,2S,6S,8S,8AR)-1-NAPHTHALENEHEPTANOIQUE
  申请人：BIOCON LTD

  公开号：WO2005019155A1

  公开（公告）日：2005-03-03

  A process for the preparation of substantially pure 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-, (beta R,delta R,1S,2S,6S,8S,8aR)- 1-Naphthaleneheptanoic acid, sodium salt is disclosed.

  揭示了一种制备基本纯的1,2,6,7,8,8a-六氢-β，δ，6-三羟基-2-甲基-8-[(2S)-2-甲基-1-羟基丁酰氧基]-，(β R，δ R，1S，2S，6S，8S，8aR)-1-萘庚酸，钠盐的方法。
• Compounds and methods to increase plasma HDL cholesterol levels and improve HDL functionality
  申请人：——

  公开号：US20020016364A1

  公开（公告）日：2002-02-07

  It has been discovered that certain selected ethers of probucol, and their pharmaceutically acceptable salts or prodrugs, are useful for increasing circulating HDL cholesterol. These compounds may also improve HDL functionality by (a) increasing clearance of cholesteryl esters, (b) increasing HDL-particle affinity for hepatic cell surface receptors or (c) increasing the half life of apoAI-HDL.

  已发现，普布考尔的某些选择性醚类化合物及其药用盐或前药对增加循环高密度脂蛋白胆固醇具有益处。这些化合物还可以通过以下方式改善高密度脂蛋白的功能：(a)增加胆固醇酯的清除，(b)增加高密度脂蛋白颗粒对肝细胞表面受体的亲和力，或者(c)增加apoAI-HDL的半衰期。
• [EN] SALT OF 1,2,6,7,8,8A-HEXAHYDRO-beta,delta,6-TRIHYDROXY-2-METHYL-8-[(2S)-2-METHYL-1-OXOBUTOXY]-, (betaR,delta R,1S,2S,6S,8S,8AR)- 1-NAPHTHALENEHEPTANOIC ACID WITH N,N-DIMETHYL-IMIDODICARBONIMIDIC DIAMIDE<br/>[FR] SEL DE L'ACIDE 1,2,6,7,8,8A-HEXAHYDRO-20050414WO03075933A1UPSHER SMITH LAB INC [US]20030918XXWO0045818A1ASTRAZENECA UK LTD [GB], et al20000810XX
  申请人：BIOCON LTD

  公开号：WO2005033067A1

  公开（公告）日：2005-04-14

  A novel compound of formula (I), a mutual salt of 1,2,6,7,8,8a-hexahydro-β,δ,6-trihydroxy-2-methyl-8-[(2s)-2-methyl-1-oxobutoxy]-, (βR,δ R,1S,2S,6S,8S,8aR)- 1-naphthaleneheptanoic acid and N,N-dimethyl- imidodicarbonimidic diamide, is disclosed. The compound of formula (I) can be used for the treatment of hyperlipidemia and hyperglycemia.

  公开了一种式为（I）的新化合物，它是1,2,6,7,8,8a-六氢-β，δ，6-三羟基-2-甲基-8-[(2s)-2-甲基-1-氧丁氧基]-，（βR，δR，1S，2S，6S，8S，8aR）-1-萘庚酸和N，N-二甲基-咪唑二碳酰亚胺的相互盐。式（I）的化合物可用于治疗高脂血症和高血糖。