1-(benzo[d]thiazol-2-yl)-5-(naphthalen-2-yl)pentan-1-one | 1283149-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(benzo[d]thiazol-2-yl)-5-(naphthalen-2-yl)pentan-1-one
• 英文别名: 1-(1,3-Benzothiazol-2-yl)-5-naphthalen-2-ylpentan-1-one
• CAS: 1283149-28-9
• 化学式: C₂₂H₁₉NOS
• 分子量: 345.465
• InChiKey: PKRTXQVTIJMLGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-萘-2-基戊酸 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 正丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 21.42h， 生成 1-(benzo[d]thiazol-2-yl)-5-(naphthalen-2-yl)pentan-1-one
  参考文献：
  名称：

  α-Ketoheterocycles Able to Inhibit the Generation of Prostaglandin E2 (PGE2) in Rat Mesangial Cells

  摘要：

  前列腺素E2（PGE2）是炎症的关键介质，因此人们已经付出了巨大的努力来开发能够调节其形成的新型药物。在这项工作中，我们介绍了各种α-酮杂环的合成，并研究它们抑制细胞水平PGE2形成的能力。合成了一系列α-酮苯并噻唑、α-酮苯并噁唑、α-酮苯并咪唑和α-酮-1,2,4-噁二唑，并进行了化学表征。评估它们在白细胞介素-1β加福尔斯科林刺激的系膜细胞中抑制PGE2生成的能力，发现了一种α-酮苯并噻唑（GK181）和一种α-酮苯并噁唑（GK491），它们能够在纳摩尔水平上抑制PGE2的生成。

  DOI：

  10.3390/biom11020275

文献信息

• 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。
• ANTIINFLAMMATORY 2-OXOTHIAZOLES
  申请人：Avexxin AS

  公开号：EP3431084A1

  公开（公告）日：2019-01-23

  A compound of formula (I) wherein X is O or S; R1 is H, OH, SH, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, halo, haloC1-6alkyl, CN, C1-6-alkyl, OC1-6alkyl, C1-6alkylCOOH, C1-6alkylCOOC1-6alkyl, C2-6-alkenyl, C3-10cycloalkyl, C6-10aryl, C1-6alkylC6-10aryl, heterocyclyl, heteroaryl, CONH2, CONHC1-6alkyl, CON(C1-6alkyl)2, OCOC1-6alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R2 is as defined for R1 or R1 and R2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R5; R3 is H, halo (preferably fluoro), or CHal3 (preferably CF3); each R5 is defined as for R1; V1 is a covalent bond or a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; M1 is absent or is a C5-10 cyclic group or a C5-15 aromatic group; and R4 is H, halo, OH, CN, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, haloC1-6alkyl, a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group, said C1-20alkyl or C2-20alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; with the proviso that the group V1M1R4 as a whole provides at least 4 backbone atoms from the C(R3) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.

  式 (I) 的化合物 其中 X 是 O 或 S； R1是H、OH、SH、硝基、NH2、NHC1-6烷基、N(C1-6烷基)2、卤素、卤代 C1-6烷基、CN、C1-6烷基、OC1-6烷基、C1-6烷基COOH、C1-6烷基COOC1-6烷基、C2-6烯基、C3-10环烷基、C6-10芳基、C1-6烷基C6-10芳基、杂环烷基、杂芳基、CONH2、CONHC1-6烷基、CON(C1-6烷基)2、OCOC1-6烷基或酸性基团，如包含羧基、磷酸基、膦酸 基、硫酸基、磺酸基或四唑基的基团； R2 如 R1 所定义，或 R1 和 R2 可共同形成一个最多被 4 个基团 R5 任选取代的 6 元芳香环； R3 是 H、卤代（最好是氟代）或 CHal3（最好是 CF3）； 每个 R5 的定义与 R1 相同； V1 是共价键或 C1-20 烷基或 C2-20 单不饱和或多不饱和烯基；所述烷基或烯基任选被选自 O、NH、N（C1-6 烷基）、S、SO 或 SO2 的一个或多个杂原子所取代； M1 不存在或为 C5-10 环状基团或 C5-15 芳香基团；以及 R4 是 H、卤素、OH、CN、硝基、NH2、NHC1-6烷基、N(C1-6烷基)2、卤代 C1-6烷基、C1-20烷基或 C2-20 单不饱和或多不饱和烯基，所述 C1-20 烷基或 C2-20 烯基任选被一个或多个选自 O、NH、N(C1-6烷基)、S、SO 或 SO2 的杂原子间隔； 但整个基团 V1M1R4 至少有 4 个来自 C（R3）基团的骨架原子； 或其盐、酯、溶剂、N-氧化物或原药； 用于治疗慢性炎症。
• 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。
• 2-oxothiazole compounds and method of using same for chronic inflammatory disorders
  申请人：Avexxin AS

  公开号：US10370344B2

  公开（公告）日：2019-08-06

  The invention provides compounds of formula (I) wherein X is O or S; R1 is H, OH, SH, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, halo, haloC1-6alkyl, CN, C1-6-alkyl, OC1-6alkyl, C1-6alkylCOOH, C1-6alkylCOOC1-6alkyl, C2-6-alkenyl, C3-10cycloalkyl, C6-10aryl, C1-6alkylC6-10aryl, heterocyclyl, heteroaryl, CONH2, CONHC1-6alkyl, CON(C1-6alkyl)2, OCOC1-6alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R2 is as defined for R1 or R1 and R2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R5; R3 is H, halo (preferably fluoro), or CHal3 (preferably CF3); each R5 is defined as for R1; V1 is a covalent bond, —O—, or a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; M1 is absent or is a C5-10 cyclic group or a C5-15 aromatic group; and R4 is H, halo, OH, CN, nitro, NH2, NHC1-6alkyl, N(C1-6alkylh, haloC1-6alkyl, a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group, said C1-20alkyl or C2-20oalkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; with the proviso that the group V1M1R4 as a whole provides at least 4 backbone atoms from the C(R3) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.

  本发明提供了式 (I) 的化合物 其中 X 是 O 或 S； R1是H、OH、SH、硝基、NH2、NHC1-6烷基、N(C1-6烷基)2、卤素、卤代C1-6烷基、CN、C1-6烷基、OC1-6烷基、C1-6烷基COOH、C1-6烷基COOC1-6烷基、C2-6烯基、C3-10环烷基、C6-10芳基、C1-6烷基C6-10芳基、杂环烷基、杂芳基、CONH2、CONHC1-6烷基、CON(C1-6烷基)2、OCOC1-6烷基或酸性基团，如包含羧基、磷酸基、膦酸 基、硫酸基、磺酸基或四唑基的基团； R2 如 R1 所定义，或 R1 和 R2 可共同形成一个最多被 4 个基团 R5 任选取代的 6 元芳香环； R3 是 H、卤代（最好是氟代）或 CHal3（最好是 CF3）； 每个 R5 的定义与 R1 相同； V1 是共价键、-O-、或 C1-20 烷基、或 C2-20 单或多元不饱和烯基；所述烷基或烯基可选择被一个或多个选自 O、NH、N（C1-6 烷基）、S、SO 或 SO2 的杂原子打断； M1 不存在或为 C5-10 环状基团或 C5-15 芳香基团；以及 R4 是 H、卤素、OH、CN、硝基、NH2、NHC1-6烷基、N(C1-6烷基h、卤代 C1-6烷基、C1-20烷基或 C2-20 单或多不饱和烯基，所述 C1-20 烷基或 C2-20 烯基任选被一个或多个选自 O、NH、N(C1-6烷基)、S、SO 或 SO2 的杂原子打断； 但整个基团 V1M1R4 至少有 4 个来自 C（R3）基团的骨架原子； 或其盐、酯、溶液剂、N-氧化物或原药；用于治疗慢性炎症。
• COMPOUND
  申请人：Kokotos George

  公开号：US20110136879A1

  公开（公告）日：2011-06-09

  The invention provides compounds of formula (I) wherein X is O or S; R 1 is H, OH, SH, nitro, NH 2 , NHC 1-6 alkyl, N(C 1-6 alkyl) 2 , halo, haloC 1-6 alkyl, CN, C 1-6 -alkyl, OC 1-6 alkyl, C 1-6 alkylCOOH, C 1-6 alkylCOOC 1-6 alkyl, C 2-6 -alkenyl, C 3-10 cycloalkyl, C 6-10 aryl, C 1-6 alkylC 6-10 aryl, heterocyclyl, heteroaryl, CONH 2 , CONHC 1-6 alkyl, CON(C 1-6 alkyl) 2 , OCOC 1-6 alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R 2 is as defined for R 1 or R 1 and R 2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R 5 ; R 3 is H, halo (preferably fluoro), or CHal 3 (preferably CF 3 ), each R 5 is defined as for R 1 ; V 1 is a covalent bond or a C 1-20 alkyl group, or C 2-20 -mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C 1-6 alkyl), S, SO, or SO 2 ; M 1 is absent or is a C 5-10 cyclic group or a C 5-15 aromatic group; and R 4 is H, halo, OH, CN, nitro, NH 2 , NHC 1-6 alkyl, N(C 1-6 alkyl) 2 , haloC 1-6 alkyl, a C 1-20 alkyl group, or C 2-20 -mono or multiply unsaturated alkenyl group, said C 1-20 alkyl or C 2-20 alkenyl groups being optionally interupted by one or more heteroatoms selected from O, NH, N(C 1-6 alkyl), S, SO, or SO 2 ; with the proviso that the group V 1 M 1 R 4 as a whole provides at least 4 backbone atoms from the C(R 3 ) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.