ethyl 2-(4-octylphenoxy)acetate | 1621517-92-7

• 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: ethyl 2-(4-octylphenoxy)acetate
• 英文别名: Ethyl 2-(4-octylphenoxyl)acetate
• CAS: 1621517-92-7
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: HKNIGVRUCOIZSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  ethyl 2-(4-octylphenoxy)acetate 在 sodium hypochlorite 、 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 sodium bromide 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 6.67h， 生成 1-(benzo[d]thiazol-2-yl)-2-(4-octylphenoxy)ethanone
  参考文献：
  名称：

  Inhibition of Group IVA Cytosolic Phospholipase A₂ by Thiazolyl Ketones in Vitro, ex Vivo, and in Vivo

  摘要：

  Group WA cytosolic phospholipase A(2) (GIVA cPLA(2)) is the rate-limiting provider of pro-inflammatory mediators in many tissues and is thus an attractive target for the development of novel anti-inflammatory agents. In this work, we present the synthesis of new thiazolyl ketones and the study of their activities in vitro, in cells, and in vivo. Within this series of compounds, methyl 2-(2-(4-octylphenoxy)acetyl)thiazole-4-carboxylate (GK470) was found to be the most potent inhibitor of GIVA cPLA(2), exhibiting an X-I(50) value of 0.011 mole fraction in a mixed micelle assay and an IC50 of 300 nM in a vesicle assay. In a cellular assay using SW982 fibroblast-like synoviocytes, it suppressed the release of arachidonic acid with an IC50 value of 0.6 mu M. In a prophylactic collagen-induced arthritis model, it exhibited an anti-inflammatory effect comparable to the reference drug methotrexate, whereas in a therapeutic model, it showed results comparable to those of the reference drug Enbrel. In both models, it significantly reduced plasma PGE(2) levels.

  DOI：

  10.1021/jm500192s
• 作为产物：
  描述：

  4-辛基酚 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以98%的产率得到ethyl 2-(4-octylphenoxy)acetate
  参考文献：
  名称：

  [EN] ANTIINFLAMMATORY AND ANTITUMOR 2-OXOTHIAZOLES AND 2-OXOTHIOPHENES COMPOUNDS
  [FR] COMPOSÉS 2-OXOTHIAZOLES ET 2-OXOTHIOPHÈNES ANTI-INFLAMMATOIRES ET ANTITUMORAUX

  摘要：

  式（I）的化合物，其中X为O、CO或S；Y为N或CH；R2和R4分别独立地为H、-(CH2)pCOOH、-(CH2)pCON(R5)2或-(CH2)pCOOC 1-6alkyI；或R2和R4一起形成与五元环融合的六元苯环；每个R1独立地选自H、卤素（例如氟或氯）、C6-10芳基、C7-12芳基烷基、C2-12烯基；OC1-2烷基、OC2-12烯基或C1-12烷基基团；每个R5为H或C1-6烷基；每个p为0至3；n为1至4；或其盐、酯、溶剂化合物、N-氧化物或前药，例如其盐。

  公开号：

  WO2014118195A1

文献信息

• [EN] ANTIINFLAMMATORY AND ANTITUMOR 2-OXOTHIAZOLES AND 2-OXOTHIOPHENES COMPOUNDS<br/>[FR] COMPOSÉS 2-OXOTHIAZOLES ET 2-OXOTHIOPHÈNES ANTI-INFLAMMATOIRES ET ANTITUMORAUX
  申请人：AVEXXIN AS

  公开号：WO2014118195A1

  公开（公告）日：2014-08-07

  A compound of formula (I) wherein X is O, C O or S; Y is N or CH; R2 and R4 are each independently H, -(CH2)pCOOH, -(CH2)pCON(R5)2 or - (CH2)pCOOC 1-6alkyI; or R2 and R4 together form a 6-membered phenyl ring fused to the five membered ring; each R1 is independently selected from H, halo (e.g. fluoro or chloro), C6-10aryl, C7-12arylalkyl, C2-12alkenyl; OC1-2 alkyl, OC2-12 aikenyl or a C1-12 alkyl group; each R5 is H or C1-6 alkyl; each p is 0 to 3; n is 1 to 4; or a salt, ester, solvate, N-oxide, or prodrug thereof, e.g. a salt thereof.

  式（I）的化合物，其中X为O、CO或S；Y为N或CH；R2和R4分别独立地为H、-(CH2)pCOOH、-(CH2)pCON(R5)2或-(CH2)pCOOC 1-6alkyI；或R2和R4一起形成与五元环融合的六元苯环；每个R1独立地选自H、卤素（例如氟或氯）、C6-10芳基、C7-12芳基烷基、C2-12烯基；OC1-2烷基、OC2-12烯基或C1-12烷基基团；每个R5为H或C1-6烷基；每个p为0至3；n为1至4；或其盐、酯、溶剂化合物、N-氧化物或前药，例如其盐。
• ANTIIFLAMMATORY AND ANTITUMOR 2-OXOTHIAZOLES ABD 2-OXOTHIOPHENES COMPOUNDS
  申请人：AVEXXIN AS

  公开号：US20150376161A1

  公开（公告）日：2015-12-31

  A compound of formula (I) wherein X is O, C═O or S; Y is N or CH; R 2 and R 4 are each independently H, —(CH 2 ) p COOH, —(CH 2 ) p CON(R 5 ) 2 or —(CH 2 ) p COOC 1-6 alkyl; or R 2 and R 4 together form a 6-membered phenyl ring fused to the five membered ring; each R 1 is independently selected from H, halo (e.g. fluoro or chloro), C 6-10 aryl, C 7-12 arylalkyl, C 2-12 alkenyl; OC 1-12 alkyl, OC 2-12 alkenyl or a C 1-12 alkyl group; each R 5 is H or C 1-6 alkyl; each p is 0 to 3; n is 1 to 4; or a salt, ester, solvate, N-oxide, or prodrug thereof, e.g. a salt thereof

  化合物的式子(I)，其中X是O，C═O或S;Y是N或CH;R2和R4各自独立地为H，—(CH2)pCOOH，—(CH2)pCON(R5)2或—(CH2)pCOOC1-6烷基;或者R2和R4共同形成一个6成员苯环融合到五成员环上;每个R1独立地选自H，卤素（例如氟或氯），C6-10芳基，C7-12芳基烷基，C2-12烯丙基;OC1-12烷基，OC2-12烯丙基或C1-12烷基;每个R5是H或C1-6烷基;每个p为0到3;n为1到4;或其盐，酯，溶剂化物，N-氧化物或前药，例如其盐。
• Anti-inflammatory and antitumor 2-oxothiazoles ABD 2-oxothiophenes compounds
  申请人：Avexxin AS

  公开号：US10259801B2

  公开（公告）日：2019-04-16

  A compound of formula (I) wherein X is O, C═O or S; Y is N or CH; R2 and R4 are each independently H, —(CH2)pCOOH, —(CH2)pCON(R5)2 or —(CH2)pCOOC1-6alkyl; or R2 and R4 together form a 6-membered phenyl ring fused to the five membered ring; each R1 is independently selected from H, halo (e.g. fluoro or chloro), C6-10aryl, C7-12arylalkyl, C2-12 alkenyl; OC1-12 alkyl, OC2-12 alkenyl or a C1-12 alkyl group; each R5 is H or C1-6 alkyl; each p is 0 to 3; n is 1 to 4; or a salt, ester, solvate, N-oxide, or prodrug thereof, e.g. a salt thereof.

  式 (I) 的化合物 其中 X 是 O、C═O 或 S； Y 是 N 或 CH； R2 和 R4 各自独立地为 H、-(CH2)pCOOH、-(CH2)pCON(R5)2 或 -(CH2)pCOOC1-6烷基；或 R2 和 R4 共同形成与五元环融合的六元苯基环； 每个 R1 独立选自 H、卤代物（如氟或氯）、C6-10 芳基、C7-12 芳烷基、C2-12 烯基、OC1-12 烷基、OC2-12 烯基或 C1-12 烷基； 每个 R5 是 H 或 C1-6 烷基 每个 p 是 0 至 3 n 为 1 至 4； 或其盐、酯、溶液、N-氧化物或原药，例如其盐。
• Anti-inflammatory and antitumor 2-oxothiazoles and 2-oxothiophenes compounds
  申请人：Avexxin AS

  公开号：US11034666B2

  公开（公告）日：2021-06-15

  A compound of formula (I) wherein X is O, C═O or S; Y is N or CH; R2 and R4 are each independently H, —(CH2)pCOOH, —(CH2)pCON(R5)2 or —(CH2)pCOOC1-6alkyl; or R2 and R4 together form a 6-membered phenyl ring fused to the five membered ring; each R1 is independently selected from H, halo (e.g. fluoro or chloro), C6-10aryl, C7-12arylalkyl, C2-12 alkenyl; OC1-12 alkyl, OC2-12 alkenyl or a C1-12 alkyl group; each R5 is H or C1-6 alkyl; each p is 0 to 3; n is 1 to 4; or a salt, ester, solvate, N-oxide, or prodrug thereof, e.g. a salt thereof.

  式 (I) 的化合物 其中 X 是 O、C═O 或 S； Y 是 N 或 CH； R2 和 R4 各自独立地为 H、-(CH2)pCOOH、-(CH2)pCON(R5)2 或 -(CH2)pCOOC1-6烷基；或 R2 和 R4 共同形成与五元环融合的六元苯基环； 每个 R1 独立选自 H、卤代物（如氟或氯）、C6-10 芳基、C7-12 芳烷基、C2-12 烯基、OC1-12 烷基、OC2-12 烯基或 C1-12 烷基； 每个 R5 是 H 或 C1-6 烷基 每个 p 是 0 至 3 n 为 1 至 4； 或其盐、酯、溶液、N-氧化物或原药，例如其盐。
• ANTIINFLAMMATORY AND ANTITUMOR 2-OXOTHIAZOLES AND 2-OXOTHIOPHENES COMPOUNDS
  申请人：Avexxin AS

  公开号：EP2951164A1

  公开（公告）日：2015-12-09