3-(4-(methylthio)phenyl)-3-oxopropanenitrile | 1344045-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-(methylthio)phenyl)-3-oxopropanenitrile
• 英文别名: 3-(4-(Methylthio)phenyl)-3-oxopropanenitrile；3-(4-methylsulfanylphenyl)-3-oxopropanenitrile
• CAS: 1344045-96-0
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: XPEZAVOWNYUZGL-UHFFFAOYSA-N

物化性质

• 沸点：
  386.4±27.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-(methylthio)phenyl)-3-oxopropanenitrile 在 吡啶 、 盐酸 、 potassium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.0h， 生成 tert-butyl {(Z)-{[4-(2-{3-acetamido-5-[4-(methylsulfonyl)phenyl]-1H-pyrazol-1-yl}ethyl)phenyl]amino}-[(tert-butoxycarbonyl)amino]methylene}carbamate
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048
• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 pyridinium hydrobromide perbromide 、 氢溴酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(4-(methylthio)phenyl)-3-oxopropanenitrile
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048

文献信息

• [EN] BICYCLIC HETEROARYL UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS<br/>[FR] COMPOSÉS D'HÉTÉROARYLE URÉE, THIOURÉE,GUANIDINE ET CYANOGUANIDINE EN TANT QU'INHIBITEURS DE LA KINASE TRKA
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2014078408A1

  公开（公告）日：2014-05-22

  Compounds of Formula I or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis and pelvic pain syndrome.

  式I化合物或其立体异构体、互变异构体或药学上可接受的盐、溶剂合物或前药，其中环A、环C和X如本文所定义，是TrkA激酶的抑制剂，并且在治疗可以用TrkA激酶抑制剂治疗的疾病中具有用处，如疼痛、癌症、炎症/炎症性疾病、神经退行性疾病、某些传染病、干燥综合征、子宫内膜异位症、糖尿病周围神经病变、前列腺炎和盆腔疼痛综合征。
• [EN] N-(ARYLALKYL)-N'-PYRAZOLYL-UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS<br/>[FR] COMPOSÉS DE N-(ARYLALKYLE)-N'-PYRAZOLYLE-URÉE, DE THIOURÉE, DE GUANIDINE ET DE CYANOGUANIDINE EN TANT QU'INHIBITEURS DE LA KINASE TRKA
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2014078331A1

  公开（公告）日：2014-05-22

  Compounds of Formula I or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C, X, Ra, Rb, Rc, Rd and n are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis or pelvic pain syndrome.

  公式I的化合物或立体异构体、互变异构体、或药用可接受的盐、溶剂化物或前药，其中环A、环C、X、Ra、Rb、Rc、Rd和n如本文所述定义，是TrkA激酶的抑制剂，可用于治疗可以用TrkA激酶抑制剂治疗的疾病，如疼痛、癌症、炎症/炎症性疾病、神经退行性疾病、某些传染病、舍格伦综合症、子宫内膜异位症、糖尿病周围神经病变、前列腺炎或骨盆疼痛综合征。
• [EN] BICYCLIC UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS USEFUL FOR THE TREATMENT OF PAIN<br/>[FR] COMPOSÉS DE THIO-URÉE, GUANIDINE, CYNOGUANIDINE ET D'URÉE BICYCLIQUES UTILES POUR LE TRAITEMENT DE LA DOULEUR
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2014078454A1

  公开（公告）日：2014-05-22

  Compounds of Formula I: or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis and pelvic pain syndrome.

  公式I的化合物：或立体异构体、互变异构体、或药用可接受的盐、溶剂化物或前药，其中环A、环C和X如本文定义，是TrkA激酶的抑制剂，可用于治疗可以用TrkA激酶抑制剂治疗的疾病，如疼痛、癌症、炎症/炎症性疾病、神经退行性疾病、某些传染病、舍格伦综合症、子宫内膜异位症、糖尿病周围神经病、前列腺炎和盆腔疼痛综合症。
• [EN] THIAZOLYL AND OXAZOLYL UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS<br/>[FR] COMPOSÉS DE THIAZOLYL-URÉE, OXAZOLYL-URÉE, THIO-URÉE, GUANIDINE ET CYANOGUANIDINE EN TANT QU'INHIBITEURS DE LA KINASE TRKA
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2014078322A1

  公开（公告）日：2014-05-22

  Compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis or pelvic pain syndrome.

  公式(I)的化合物或立体异构体、互变异构体、或其药物可接受的盐、溶剂化物或前药，其中环A、环C和X如本文定义，是TrkA激酶的抑制剂，并且可用于治疗可以用TrkA激酶抑制剂治疗的疾病，例如疼痛、癌症、炎症、神经退行性疾病、某些传染病、干燥综合征、子宫内膜异位症、糖尿病周围神经病变、前列腺炎或骨盆疼痛综合征。
• [EN] N-(MONOCYCLIC ARYL),N'-PYRAZOLYL-UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS<br/>[FR] COMPOSÉS DE N-ARYLE MONOCYCLIQUES, N'-PYRAZOLYL-URÉE, THIOURÉE, GUANIDINE ET CYANOGUANIDINE UTILES COMME INHIBITEURS DE TRKA KINASE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2014078325A1

  公开（公告）日：2014-05-22

  Compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis or pelvic pain syndrome.

  化合物的公式(I)或其立体异构体、互变异构体、或其药学上可接受的盐、溶剂合物或前药，其中环A、环C和X如本文所定义，是TrkA激酶的抑制剂，并且在治疗可以用TrkA激酶抑制剂治疗的疾病中具有用处，如疼痛、癌症、炎症/炎症性疾病、神经退行性疾病、某些传染病、干燥综合征、子宫内膜异位症、糖尿病周围神经病变、前列腺炎或盆腔疼痛综合征。