ethyl 5-methoxyimidazo<2,1-b>benzothiazole-2-carboxylate | 113508-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: ethyl 5-methoxyimidazo<2,1-b>benzothiazole-2-carboxylate
• 英文别名: ethyl 12-methoxy-7-thia-2,5-diazatricyclo[6.4.0.0^2,6]dodeca-1(8),3,5,9,11-pentaene-4-carboxylate；5-Methoxyimidazo[2,1-b]benzothiazole-2-carboxylic acid ethyl ester；ethyl 8-methoxyimidazo[2,1-b][1,3]benzothiazole-2-carboxylate
• CAS: 113508-94-4
• 化学式: C₁₃H₁₂N₂O₃S
• 分子量: 276.316
• InChiKey: PCKNOZQFVUGRDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-methoxyimidazo<2,1-b>benzothiazole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以85%的产率得到12-methoxy-7-thia-2,5-diazatricyclo[6.4.0.0^2,6]dodeca-1(8),3,5,9,11-pentaene-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009
• 作为产物：
  描述：

  2-氨基-4-甲氧基苯并噻唑 、 3-溴丙酮酸乙酯 在 乙醇 作用下， 生成 ethyl 5-methoxyimidazo<2,1-b>benzothiazole-2-carboxylate
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009

文献信息

• [EN] IMIDAZO[2,1-B]THIAZOLE AND 5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLE DERIVATIVES USEFUL AS S100-INHIBITORS<br/>[FR] DÉRIVÉS IMIDAZO[2,1-B]THIAZOLE ET 5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLE UTILES EN TANT QU'INHIBITEURS DE S100
  申请人：ACTIVE BIOTECH AB

  公开号：WO2016042172A1

  公开（公告）日：2016-03-24

  A compound of formula (I) or a pharmaceutically acceptable salt thereof. The compound is useful for use in the treatment of cancer, an inflammatory disorder,an autoimmunity disorder or a neurodegenerative disorder.

  化合物的化学式（I）或其药用盐。该化合物可用于治疗癌症、炎症性疾病、自身免疫性疾病或神经退行性疾病。
• Imidazo[2,1-B]thiazole and 5,6-dihydroimidazo[2,1-B]thiazole derivatives useful as S100-inhibitors
  申请人：Active Biotech AB

  公开号：US10385069B2

  公开（公告）日：2019-08-20

  A compound of formula (I) or a pharmaceutically acceptable salt thereof. The compound is useful for use in the treatment of cancer, an inflammatory disorder, an autoimmunity disorder or a neurodegenerative disorder.

  式 (I) 的化合物或其药学上可接受的盐。该化合物可用于治疗癌症、炎症性疾病、自身免疫性疾病或神经退行性疾病。
• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——
• IMIDAZO[2,1-B]THIAZOLE AND 5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLE DERIVATIVES USEFUL AS S100-INHIBITORS
  申请人：Active Biotech AB

  公开号：US20180282348A1

  公开（公告）日：2018-10-04

  A compound of formula (I) or a pharmaceutically acceptable salt thereof. The compound is useful for use in the treatment of cancer, an inflammatory disorder, an autoimmunity disorder or a neurodegenerative disorder.
• Synthesis and benzodiazepine receptor binding of some imidazoand pyrimido[2,1-b]benzothiazoles
  作者：G Trapani、M Franco、A Latrofa、A Carotti、G Gerichi、M Serra、G Biggio、G Liso

  DOI：10.1016/0223-5234(96)89553-5

  日期：1996.1

  A series of substituted imidazo[2,1-b]benzothiazoles 2a-u was synthesized and the compounds evaluated for their affinity at the central benzodiazepine receptors. Substitution at the 7-position generally resulted in a decreased ligand affinity whereas a significant increase was observed for 5-substituted compounds. The intrinsic efficacy of selected high-affinity ligands 2j,k,q, as well as some previously reported pyrimido[2,1-b]benzothiazoles 1, was measured in vitro through the determination of the GABA ratio and [S-35]TBPS displacement. Consistent with a partial inverse agonist profile, the benzothiazole derivatives 2j,k,q increased [S-35]TBPS binding. For compounds 1c and 1d, a discrepancy between GABA ratio and [S-35]TBPS binding data was observed. Only the latter assay was in full agreement with the pharmacological data, which indicated an inverse agonist and a partial agonist profile for 2k,q and 1c,d respectively. The affinity and intrinsic activity data of compounds 1c,d and 2j,k,q are discussed in the light of the recently proposed pharmacophore model by Skolnick/Cook; in particular, the agonistic activity of 1c,d is interpreted on the basis of a possible interaction of substitutents in position 6 with the receptors lipophilic area L3 of Skolnick/Cook, whereas the observed inverse agonist profile of 2j,k,q is explained taking into account their structural analogy with the well known proconvulsant beta-CCE.