2-chloro-6-(1H-pyrrol-1-yl)benzonitrile | 418762-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-chloro-6-(1H-pyrrol-1-yl)benzonitrile
• 英文别名: 2-chloro-6-(1H-pyrrol-1-yl)-benzonitrile；2-chloro-6-pyrrol-1-ylbenzonitrile
• CAS: 418762-89-7
• 化学式: C₁₁H₇ClN₂
• 分子量: 202.643
• InChiKey: OSROJQITBWZVDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-6-(1H-pyrrol-1-yl)benzonitrile 在 盐酸 、 dimethyl sulfide borane 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 43.5h， 生成 2-(1H-pyrrol-1-yl)-6-chlorobenzylamine
  参考文献：
  名称：

  通过 PIII/PV 催化驱动递归脱水：通过连续的 C-N 和 C-C 键形成环化胺和羧酸

  摘要：

  报道了一种通过有机磷 PIII/PV 氧化还原催化将胺和羧酸环化形成药学相关氮杂杂环的方法。该方法使用磷烷催化剂以及温和的溴鎓氧化剂和末端氢硅烷还原剂，通过催化溴鏻中间体的串联作用来驱动连续的 C-N 和 C-C 键形成脱水事件。这些结果证明了 PIII/PV 氧化还原催化的能力，能够实现重复的氧化还原中性转化，以补充 PIII/PV 对的共同还原驱动力。

  DOI：

  10.1021/jacs.9b06277
• 作为产物：
  描述：

  2,5-二乙氧基四氢呋喃 、 2-氨基-6-氯苯甲腈 在 溶剂黄146 作用下， 反应 0.5h， 生成 2-chloro-6-(1H-pyrrol-1-yl)benzonitrile
  参考文献：
  名称：

  Pyrrolo[1,2-a][1,4]benzodiazepine: A novel class of non-azole anti-dermatophyte anti-fungal agents

  摘要：

  Broad screening revealed compound la to be a novel anti-fungal agent with high specificity towards dermatophytes. The anti-fungal structure-activity relationship of this novel class of 5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines is described together with its mode of action that appeared to be the inhibition of squalene epoxidase. Preliminary in vivo results of the most active compounds are also reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.007

文献信息

• [EN] NOVEL ANTIFUNGAL 5,6-DIHYDRO-4H-PYRROLO[1,2-a][1,4]- BENZODIAZEPINES AND 6H-PYRROLO[1,2-a][1,4]BENZODIAZEPINES SUBSTITUTED WITH BICYCLIC BENZENE DERIVATIVES<br/>[FR] NOUVELLES 5,6-DIHYDRO-4H-PYRROLO-[1,2-A][1,4]BENZODIAZÉPINES ET 6H-PYRROLO[1,2-A][1,4]BENZODIAZÉPINES ANTIFONGIQUES SUBSTITUÉES PAR DES DÉRIVÉS BICYCLIQUES DU BENZÈNE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012084804A1

  公开（公告）日：2012-06-28

  The present invention is concerned with novel antifungal 5,6-dihydro-4H-pyrrolo- [1,2-a][1,4]benzodiazepines and 6H-pyrrolo[1,2-a][1,4]benzodiazepines substituted with bicyclic benzene derivatives of Formula (I) wherein R1, R2, R3, R4, R5, R6 and R7 have the meaning defined in the claims. The compounds according to the present invention are active mainly against dermatophytes and systemic fungal infections. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及一种新型抗真菌5,6-二氢-4H-吡咯- [1,2-a][1,4]苯并二氮杂环和6H-吡咯- [1,2-a][1,4]苯并二氮杂环，其被取代为公式（I）中的双环苯衍生物，其中R1，R2，R3，R4，R5，R6和R7具有权利要求中定义的含义。根据本发明的化合物主要对抗皮肤癣和系统性真菌感染具有活性。该发明还涉及制备这种新型化合物的工艺、含有该化合物作为活性成分的药物组合物以及将该化合物用作药物的用途。
• [EN] NOVEL ANTIFUNGAL 5,6-DIHYDRO-4H-PYRROLO[1,2-a][1,4]BENZO- DIAZEPINES AND 6H-PYRROLO[1,2-a][1,4]BENZODIAZEPINES SUBSTITUTED WITH HETEROCYCLIC DERIVATIVES<br/>[FR] NOUVELLES 5,6-DIHYDRO-4H-PYRROLO[1,2-A][1,4]BENZODIAZÉPINES ET 6H-PYRROLO[1,2-A][1,4]BENZODIAZÉPINES SUBSTITUÉES PAR DES DÉRIVÉS HÉTÉROCYCLIQUES ANTIFONGIQUES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012150305A1

  公开（公告）日：2012-11-08

  The present invention is concerned with novel antifungal 5,6-dihydro-4H-pyrrolo- [1,2-a][1,4]benzodiazepines and 6H-pyrrolo[1,2-a][1,4]benzodiazepines substituted with heterocyclic derivatives of Formula (I) wherein R1, R2, R3, R4 and Het have the meaning defined in the claims. The compounds according to the present invention are active mainly against dermatophytes and systemic fungal infections. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及一种新型抗真菌5,6-二氢-4H-吡咯并[1,2-a][1,4]苯二氮杂环和6H-吡咯并[1,2-a][1,4]苯二氮杂环，其被杂环衍生物取代的化合物，其化学结构如下所示（I）式，其中R1、R2、R3、R4和Het在权利要求中定义了含义。根据本发明的化合物主要对皮肤真菌和全身真菌感染具有活性。本发明还涉及制备这种新型化合物的方法，包括将这些化合物作为活性成分的药物组合物以及将这些化合物用作药物的用途。
• NOVEL ANTIFUNGAL 5,6-DIHYDRO-4H-PYRROLO[1,2-a][1,4]BENZO-DIAZEPINES AND 6H-PYRROLO[1,2-a][1,4]BENZODIAZEPINES SUBSTITUTED WITH HETEROCYCLIC DERIVATIVES
  申请人：Meerpoel Lieven

  公开号：US20140045827A1

  公开（公告）日：2014-02-13

  The present invention is concerned with novel antifungal 5,6-dihydro-4H-pyrrolo-[1,2-a][1,4]benzodiazepines and 6H-pyrrolo[1,2-a][1,4]benzodiazepines substituted with heterocyclic derivatives of Formula (I) wherein R 1 , R 2 , R 3 , R 4 and Het have the meaning defined in the claims. The compounds according to the present invention are active mainly against dermatophytes and systemic fungal infections. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及一种新型抗真菌5,6-二氢-4H-吡咯并-[1,2-a][1,4]苯二氮杂环和6H-吡咯并[1,2-a][1,4]苯二氮杂环，其取代有Formula (I)中的杂环衍生物的R1、R2、R3、R4和Het的含义如权利要求中所定义。根据本发明的化合物主要对抗皮肤真菌和全身真菌感染有效。本发明还涉及制备这种新型化合物的方法，含有该化合物作为活性成分的药物组合物，以及将该化合物用作药物的用途。
• NOVEL ANTIFUNGAL 5,6-DIHYDRO-4-[(DIFLUOROETHYL)PHENYL]-4H-PYRROLO[1,2-a][1,4]BENZODIAZEPINE AND 4-(DIFLUOROETHYL)PHENYL-6H-PYRROLO[1,2-a][1,4]BENZODIAZEPINE DERIVATIVES
  申请人：Meerpoel Lieven

  公开号：US20130085136A1

  公开（公告）日：2013-04-04

  The present invention concerns novel compounds of Formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meaning defined in the claims. The compounds according to the present invention are active mainly against dermatophytes and systemic fungal infections. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及式(I)的新化合物：其中R1、R2、R3、R4、R5和R6的含义如权利要求所定义。根据本发明，这些化合物主要对真菌感染和系统真菌感染具有活性。本发明还涉及制备这些新化合物的方法、包含这些化合物作为活性成分的制药组合物以及将这些化合物用作药物的用途。
• [EN] NOVEL ANTIFUNGAL 5,6-DIHYDRO-4-[(DIFLUOROETHYL)PHENYL]-4H-PYRROLO[1,2-a][1,4]BENZODIAZEPINE AND 4-(DIFLUOROETHYL)PHENYL-6H-PYRROLO[1,2-a][1,4]BENZODIAZEPINE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS ANTIFONGIQUES 5,6-DIHYDRO-4-[(DIFLUOROÉTHYL)PHÉNYL]-4H-PYRROLO[1,2-A][1,4]BENZODIAZÉPINE ET 4-(DIFLUOROÉTHYL)PHÉNYL-6H-PYRROLO[1,2-A][1,4]BENZODIAZÉPINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011154298A1

  公开（公告）日：2011-12-15

  The present invention concerns novel compounds of Formula (I) wherein R1, R2, R3, R4, R5 and R6 have the meaning defined in the claims. The compounds according to the present invention are active mainly against dermatophytes and systemic fungal infections. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及公式（I）的新化合物，其中R1、R2、R3、R4、R5和R6具有权利要求书中定义的含义。根据本发明，这些化合物主要对皮肤真菌和全身真菌感染具有活性。本发明还涉及制备这些新化合物的方法，包含该化合物作为活性成分的制药组合物，以及将该化合物作为药物使用的用途。