ethyl 4-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate | 99247-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: ethyl 4-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate
• 英文别名: Ethyl-4-hydroxy-3-methylbenzothiophene-2-carboxylate；Ethyl 4-hydroxy-3-methyl-1-benzothiophene-2-carboxylate
• CAS: 99247-06-0
• 化学式: C₁₂H₁₂O₃S
• 分子量: 236.291
• InChiKey: WJUHWLJTGCYHOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 sodium hydrogensulfite 、 N-甲基吗啉氧化物 、 sodium hydroxide 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,3'-(ethane-1,2-diylbis(5-aminoformyl-1H-benzo[d]imidazole-1,2-diyl))bis(4-methoxybenzo[b]thiophene-2-carboxylic acid)
  参考文献：
  名称：

  [EN] BENZOTHIOPHENE, THIENOPYRIDINE AND THIENOPYRIMIDINE DERIVATIVES FOR THE MODULATION OF STING
  [FR] DÉRIVÉS DE BENZOTHIOPHÈNE, DE THIÉNOPYRIDINE ET DE THIÉNOPYRIMIDINE POUR LA MODULATION DE STING

  摘要：

  式（I）的化合物：其中：Y为（CH2）n，其中n为2至4；W1和W11分别选择自OH和ORP，其中RP为Me或Et。

  公开号：

  WO2021009365A1
• 作为产物：
  描述：

  Ethyl(2-aceto-3-thiophenoxy)acetate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 ethyl 4-hydroxy-3-methylbenzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene

  摘要：

  公式I的化合物：##STR1##及其药理可接受的盐是白三烯生物合成的抑制剂。这些化合物抑制哺乳动物的5-脂氧合酶酶，从而阻止了花生四烯酸转化为白三烯的代谢。因此，这些化合物在治疗哮喘、过敏性疾病、炎症、皮肤病和某些心血管疾病方面是有用的。

  公开号：

  US04663347A1

文献信息

• [EN] SUBSTITUTED CONDENSED THIOPHENES AS MODULATORS OF STING<br/>[FR] THIOPHÈNES CONDENSÉS SUBSTITUÉS UTILISÉS EN TANT QUE MODULATEURS DE STING
  申请人：CTXT PTY LTD

  公开号：WO2019219820A1

  公开（公告）日：2019-11-21

  A compound of formula (I), wherein: R1 is selected from (i) H, (ii) C3-6cycloalkyl, (iii) C3-7heterocyclyl optionally substituted with a group selected from: methyl and ester, and (iv) linear or branched C1-4alkyl optionally substituted with a group selected from: alkoxy, amino, amido, acylamido, acyloxy, alkyl carboxyl ester, alkyl carbamoyl, alkyl carbamoyl ester, phenyl, phosphonate ester, C3-7heterocyclyl optionally substituted with a group selected from methyl and oxo, and a naturally occurring amino acid, optionally N-substituted with a group selected from methyl, acetyl and boc; A1 is CRA or N; A2 is CRB or N; A3 is CRC or N; A4 is CRD or N; where no more than two of A1, A2, A3, and A4 may be N; one or two of RA, RB, RC, and RD, (if present) are selected from H, F, Cl, Br, Me, CF3, cyclopropyl, cyano, OMe, OEt, CH2OH, CH2OMe and CH2NMe2; the remainder of RA, RB, RC, and RD, (if present) are H; Y is O, NH or CH2; RY is selected from: (RYA) and (RYB).

  化合物的化学式（I），其中：R1选自（i）H，（ii）C3-6环烷基，（iii）C3-7杂环烷基，可选择地取代为：甲基和酯，以及（iv）线性或支链C1-4烷基，可选择地取代为：烷氧基，氨基，酰胺基，酰氧基，烷基羧酯，烷基氨基，烷基氨基酯，苯基，磷酸酯，C3-7杂环烷基，可选择地取代为甲基和氧代基，以及一种天然氨基酸，可选择地N-取代为：甲基，乙酰基和boc；A1为CRA或N；A2为CRB或N；A3为CRC或N；A4为CRD或N；其中A1，A2，A3和A4中最多有两个可以是N；RA，RB，RC和RD中的一个或两个（如果存在）选自H，F，Cl，Br，Me，CF3，环丙基，氰基，OMe，OEt， OH， OMe和 NMe2；RA，RB，RC和RD的其余部分（如果存在）为H；Y为O，NH或CH2；RY选自：（RYA）和（RYB）。
• Lipoxygenase inhibitors
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0146243A1

  公开（公告）日：1985-06-26

  Compounds of the general Formula I: wherein Z is a bond, CR14=CR15 or CHR14-CHR15; X is O, S, SO, or S02 R1, R2, R3, R4, T, V are as defined in the prescription; and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders. The compounds are made into suitable pharmaceutical compositions for administration to patients. Certain of the compounds are novel.

  通式 I 的化合物：其中 Z 是键、CR14=CR15 或 CHR14-CHR15；X 是 O、S、SO 或 S02 R1、R2、R3、R4、T、V 如处方中所定义；及其药学上可接受的盐是白三烯生物合成的抑制剂。 这些化合物可抑制哺乳动物的 5-脂氧合酶，从而阻止花生四烯酸代谢为白三烯。 因此，这些化合物可用于治疗哮喘、过敏性疾病、炎症、皮肤病和某些心血管疾病。 这些化合物可制成适当的药物组合物给患者用药。 某些化合物是新型的。
• SUBSTITUTED CONDENSED THIOPHENES AS MODULATORS OF STING
  申请人：CTXT PTY LIMITED

  公开号：US20210214333A1

  公开（公告）日：2021-07-15

  A compound of formula (I), wherein R 1 is selected from (i) H, (ii) C 3-6 cycloalkyl, (iii) C 3-7 heterocyclyl optionally substituted with a group selected from: methyl and ester, and (iv) linear or branched C 1-4 alkyl optionally substituted with a group selected from: alkoxy, amino, amido, acylamido, acyloxy, alkyl carboxyl ester, alkyl carbamoyl, alkyl carbamoyl ester, phenyl, phosphonate ester, C 3-7 heterocyclyl optionally substituted with a group selected from methyl and oxo, and a naturally occurring amino acid, optionally N-substituted with a group selected from methyl, acetyl and boc; A 1 is CR A or N; A 2 is CR B or N; A 3 is CR C or N; A 4 is CR D or N; where no more than two of A 1 , A 2 , A 3 , and A 4 may be N; one or two of R A , R B , R C , and R D , (if present) are selected from H, F, Cl, Br, Me, CF 3 , cyclopropyl, cyano, OMe, OEt, CH 2 OH, CH 2 OMe and CH 2 NMe 2 ; the remainder of R A , R B , R C , and R D , (if present) are H; Y is O, NH or CH 2 ; R Y is selected from: (RYA) and (RYB).
• BENZOTHIOPHENE, THIENOPYRIDINE AND THIENOPYRIMIDINE DERIVATIVES FOR THE MODULATION OF STING
  申请人：CTXT PTY LIMITED

  公开号：US20220389032A1

  公开（公告）日：2022-12-08

  A compound of formula (I): wherein: Y is (CH2)n, where n is from 2 to 4; W1 and W11 are independently selected from OH and ORP, where RP is Me or Et.
• US4663347A
  申请人：——

  公开号：US4663347A

  公开（公告）日：1987-05-05