4-(2-chlorophenyl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile | 120517-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(2-chlorophenyl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 4-(2-thienyl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile；3-Quinolinecarbonitrile, 1,2,5,6,7,8-hexahydro-4-(2-thienyl)-2-thioxo-；2-sulfanylidene-4-thiophen-2-yl-5,6,7,8-tetrahydro-1H-quinoline-3-carbonitrile
• CAS: 120517-52-4
• 化学式: C₁₄H₁₂N₂S₂
• 分子量: 272.395
• InChiKey: YFPLWQQSRJQHQF-UHFFFAOYSA-N

物化性质

• 熔点：
  269-271 °C (decomp)
• 沸点：
  450.0±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-chlorophenyl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile 在 氢氧化钾 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 4-hydroxy-11-(thiophen-2-yl)-7,8,9,10-tetrahydropyrido[2',3':4,5]thieno[2,3-b]quinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis of substituted 4-hydroxy-1H-thieno[2,3-b;4,5-b′]dipyridin-2-ones

  摘要：

  Substituted 4-hydroxy-1 H-thieno[2,3-b;4,5-b']dipyridin-2-ones were prepared by the reactions of 3-cyanopyridine-2(1 H)-thiones with alkyl 4-chloroacetoacetates and by intramolecular cyclization of alkyl 4-(2-pyridylthio)acetoacetates or alkyl 3-(3-aminothieno[2,3-b]pyridin-2-yl)-3-oxopropionates under the action of bases.

  DOI：

  10.1007/bf02494687
• 作为产物：
  描述：

  (2E)-2-(噻吩-2-基亚甲基)环己酮 、 2-氰基硫代乙酰胺 在 potassium carbonate 、 sulfur 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以92%的产率得到4-(2-chlorophenyl)-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  [DE] INHIBITOREN DER PHOSPHODIESTERASE 4 UND TNFa-FREISETZUNG
  [EN] SUBSTITUTED PYRIDO[3', 2': 4, 5]THIENO[3,2-D]PYRIMIDINES AND PYRIDO[3', 2': 4, 5]FURO[3, 2, D]PYRIMIDINES USED AS INHIBITORS OF THE PDE-4 AND/OR THE RELEASE OF TNF$G(A)
  [FR] PYRIDO[3',2':4,5]THIENO[3,2-D]PYRIMIDINES ET PYRIDO[3',2':4,5]FURO[3,2-D]PYRIMIDINES SUBSTITUEES UTILISEES COMME INHIBITEURS DE LA PDE 4 ET DE LA LIBERATION DU TNF$G(A)

  摘要：

  该发明涉及以下一般式(I)的化合物；a, 1 b, 1 c和1 d。其制备方法，含有这些化合物和/或可由其制备的生理相容性盐和/或其溶剂化合物的药物制剂，以及这些化合物、其盐或溶剂化合物作为磷酸二酯酶4的抑制剂的药用。这些化合物作为治疗通过抑制磷酸二酯酶4和/或TNFα释放所致的疾病的药物，例如在淋巴细胞、嗜酸性粒细胞和嗜碱性粒细胞、巨噬细胞和肥大细胞中，具有积极影响。

  公开号：

  WO2006010567A1

文献信息

• Synthesis of 4-alkyl(aryl, hetaryl)-2-thioxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles and their derivatives by cross-recyclization of 4-alkyl(aryl, hetaryl)-2,6-diamino-4H-thiopyran-3,5-dicarbonitriles with 4-(cyclohex-1-en-1-yl)-morpholine, alkyl halides, and cyclohexanone
  作者：V. D. Dyachenko、A. D. Dyachenko

  DOI：10.1134/s1070428008030172

  日期：2008.3

  Cross recyclization of 4-substituted 2,6-diamino-4H-thiopyran-3,5-dicarbonitriles with 4-(cyclohex-1-en-1-yl)morpholine, alkyl halides, and cyclohexanone gave the corresponding substituted 2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitriles, 2-alkylsulfanyl-5,6,7,8-tetrahydroquinoline-3-carbonitriles, 3-amino-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxamides, and 4-oxo-2,2-pentamethylene-1,2,3,4,7,8,9,10-octahydropyrimido[4′,5′:4,5]thieno[2,3-b]quinolines. The structure of 3-(4-bromophenyl)-2,2-pentamethylene-11-(2-thienyl)-1,2,3,4,7,8,9,10-octahydropyrimido[4′,5′:4,5]thieno[2,3-b]quinoline was proved by X-ray analysis.

  4-取代的2,6-二氨基-4H-噻吡啶-3,5-二腈与4-(环己烯-1-基)吗啉、烷基卤化物和环己酮进行交叉重环化反应，得到了相应的取代2-硫代-1,2,5,6,7,8-六氢喹啉-3-腈、2-烷基硫代-5,6,7,8-四氢喹啉-3-腈、3-氨基-5,6,7,8-四氢噻吡啶[2,3-b]喹啉-2-氨基甲酸酯，以及4-氧-2,2-戊五烯-1,2,3,4,7,8,9,10-八氢嘧啶[4′,5′:4,5]噻吡啶[2,3-b]喹啉。3-(4-溴苯基)-2,2-戊五烯-11-(2-噻吡啶基)-1,2,3,4,7,8,9,10-八氢嘧啶[4′,5′:4,5]噻吡啶[2,3-b]喹啉的结构通过X射线分析得到了证明。
• [EN] ACETYL-COA CARBOXYLASE MODULATORS<br/>[FR] MODULATEURS DE L'ACÉTYL-COA CARBOXYLASE
  申请人：MONSANTO TECHNOLOGY LLC

  公开号：WO2014201326A1

  公开（公告）日：2014-12-18

  Provided herein are compounds that exhibit activity as acetyl-CoA carboxylase modulators (e.g., inhibitors) and are useful, for example, in methods for the control of fungal pathogens in plants.

  本文提供的化合物表现出作为乙酰辅酶A羧化酶调节剂（例如抑制剂）的活性，并且在例如控制植物中真菌病原体的方法中是有用的。
• SUBSTITUTED PYRIDO [3', 2': 4, 5] THIENO [3, 2-D] PYRIMIDINES AND PYRIDO [3', 2': 4, 5] FURO [3, 2-D] PYRIMIDINES USED AS INHIBITORS OF THE PDE-4 AND/OR THE RELEASE OF TNF-ALPHA
  申请人：Reichelt Claudia

  公开号：US20080160028A1

  公开（公告）日：2008-07-03

  The invention relates to compounds of general formula (I); 1a, 1 b, 1 c and 1 d. The invention also relates to a method for the production thereof, pharmaceutical preparations containing said compounds and/or physiologically compatible salts thereof which can be produced therefrom and/or solvates thereof, and to the pharmaceutical use of said compounds, salts or solvates thereof as inhibitors of phosphodiesterase 4. The compounds comprise active ingredients for the treatment of diseases which can have a positive influence by inhibiting the activity of phosphodiesterase 4 and/or TNFα-release, for example, in lymphocytes, eosinophile and basophile granulocytes, macrophages and mastocytes.

  本发明涉及通式（I）的化合物，其中包括1a、1b、1c和1d。本发明还涉及其生产方法，包含所述化合物和/或可由其制备的生理兼容盐和/或溶剂化物的药物制剂，以及所述化合物、盐或溶剂化物作为磷酸二酯酶4的抑制剂的药物用途。这些化合物包含治疗疾病的活性成分，通过抑制磷酸二酯酶4和/或TNFα释放的活性，例如在淋巴细胞、嗜酸性粒细胞和嗜碱性粒细胞、巨噬细胞和肥大细胞中产生正面影响。
• Substituted pyrido [3′, 2′: 4, 5] thieno [3, 2-D] pyrimidines and pyrido [3′, 2′: 4, 5] furo [3, 2-D] pyrimidines used as inhibitors of the PDE-4 and/or the release of TNF-ALPHA
  申请人：The Medicines Company (Leipzig) GmbH

  公开号：US08058285B2

  公开（公告）日：2011-11-15

  The invention relates to compounds of general formula (I); 1a, 1 b, 1 c and 1 d. The invention also relates to a method for the production thereof, pharmaceutical preparations containing said compounds and/or physiologically compatible salts thereof which can be produced therefrom and/or solvates thereof, and to the pharmaceutical use of said compounds, salts or solvates thereof as inhibitors of phosphodiesterase 4. The compounds comprise active ingredients for the treatment of diseases which can have a positive influence by inhibiting the activity of phosphodiesterase 4 and/or TNFα-release, for example, in lymphocytes, eosinophile and basophile granulocytes, macrophages and mastocytes.

  本发明涉及通式(I)的化合物，其中1a、1b、1c和1d。本发明还涉及其制备方法，含有该化合物和/或可从中产生的生理相容盐和/或溶剂化物的制药制剂，以及该化合物、盐或溶剂化物作为磷酸二酯酶4的抑制剂的药物用途。该化合物包含用于治疗可以通过抑制磷酸二酯酶4和/或TNFα释放的活性成分，例如在淋巴细胞、嗜酸性粒细胞和嗜碱性粒细胞、巨噬细胞和肥大细胞中。
• SUBSTITUTED PYRIDO [3', 2': 4, 5] THIENO [3, 2-D] PYRIMIDINES AND PYRIDO [3', 2': 4, 5] FURO [3, 2-D] PYRIMIDINES USED AS INHIBITORS OF THE PDE-4 AND/OR THE RELEASE OF TNF-alpha
  申请人：Reichelt Claudia

  公开号：US20120094987A1

  公开（公告）日：2012-04-19

  The invention relates to compounds of general formula (I); 1a, 1b, 1c and 1d. The invention also relates to a method for the production thereof, pharmaceutical preparations containing said compounds and/or physiologically compatible salts thereof which can be produced therefrom and/or solvates thereof, and to the pharmaceutical use of said compounds, salts or solvates thereof as inhibitors of phosphodiesterase 4. The compounds comprise active ingredients for the treatment of diseases which can have a positive influence by inhibiting the activity of phosphodiesterase 4 and/or TNFα-release, for example, in lymphocytes, eosinophile and basophile granulocytes, macrophages and mastocytes.

  本发明涉及一般式（I）的化合物，包括1a、1b、1c和1d。本发明还涉及生产这些化合物的方法，含有该化合物和/或可由其制备的生理相容盐和/或溶剂化物的制药制剂，以及该化合物、盐或溶剂化物作为磷酸二酯酶4的抑制剂的药物用途。这些化合物包含用于通过抑制磷酸二酯酶4和/或TNFα释放的活性成分治疗疾病的，例如淋巴细胞、嗜酸性粒细胞和嗜碱性粒细胞、巨噬细胞和肥大细胞等。