4-bromo-1-chloro-5-nitroisoquinoline | 18203-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-bromo-1-chloro-5-nitroisoquinoline
• 英文别名: 4-bromo-1-chloro-5-nitro-isoquinoline；1-Chlor-4-brom-5-nitro-isochinolin
• CAS: 18203-70-8
• 化学式: C₉H₄BrClN₂O₂
• 分子量: 287.5
• InChiKey: ODNWMKOLHPHFAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-1-chloro-5-nitroisoquinoline 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 sodium 作用下， 以 1,4-二氧六环 为溶剂， 反应 32.0h， 生成 1-methoxy-5-nitro-4-phenylaminoisoquinoline
  参考文献：
  名称：

  的4 -烷基- ，4-芳基-和4-芳基氨基-5-氨基异喹啉-1-酮和一个新的PARP-2选择性抑制剂的鉴定合成†

  摘要：

  对取代异喹啉-1-酮的浓厚兴趣与 5-氨基异喹啉-1-酮（5-AIQ）作为药物表明需要高效，直接地合成4,5-二取代的自行车。溴化5-硝基异喹啉-1-酮 给了 4-溴-5-硝基异喹啉-1-酮但是这个或5-氨基-4-溴异喹啉-1-酮都不参与Pd催化的偶联。然而，内酰胺作为1-甲氧基和1-苄氧基-4-溴-5-硝基异喹啉的保护，使Stille，Suzuki和Buchwald-Hartwig偶联反应的收率很高，对电子需求不敏感，并且对空间中的大量空间不敏感。芳基硼酸。锂化4-溴-1-甲氧基-5-硝基异喹啉 并用淬火 碘甲烷 给了 1-甲氧基-4-甲基-5-硝基异喹啉产量低。1-甲氧基-4-取代的5-硝基异喹啉的去甲基溴化氢 得到4-取代的5-硝基异喹啉-1-酮，而同时还原5-硝基则实现氢解脱苄基作用。 5-氨基-4-（4-三氟甲基苯基）异喹啉-1-酮 被确定为一种新型的高效选择性聚（ADP-核糖）聚合酶2（PARP-2）抑制剂。

  DOI：

  10.1039/c0ob00665c
• 作为产物：
  描述：

  4-bromo-5-nitroisoquinolin-1-one 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以89%的产率得到4-bromo-1-chloro-5-nitroisoquinoline
  参考文献：
  名称：

  的4 -烷基- ，4-芳基-和4-芳基氨基-5-氨基异喹啉-1-酮和一个新的PARP-2选择性抑制剂的鉴定合成†

  摘要：

  对取代异喹啉-1-酮的浓厚兴趣与 5-氨基异喹啉-1-酮（5-AIQ）作为药物表明需要高效，直接地合成4,5-二取代的自行车。溴化5-硝基异喹啉-1-酮 给了 4-溴-5-硝基异喹啉-1-酮但是这个或5-氨基-4-溴异喹啉-1-酮都不参与Pd催化的偶联。然而，内酰胺作为1-甲氧基和1-苄氧基-4-溴-5-硝基异喹啉的保护，使Stille，Suzuki和Buchwald-Hartwig偶联反应的收率很高，对电子需求不敏感，并且对空间中的大量空间不敏感。芳基硼酸。锂化4-溴-1-甲氧基-5-硝基异喹啉 并用淬火 碘甲烷 给了 1-甲氧基-4-甲基-5-硝基异喹啉产量低。1-甲氧基-4-取代的5-硝基异喹啉的去甲基溴化氢 得到4-取代的5-硝基异喹啉-1-酮，而同时还原5-硝基则实现氢解脱苄基作用。 5-氨基-4-（4-三氟甲基苯基）异喹啉-1-酮 被确定为一种新型的高效选择性聚（ADP-核糖）聚合酶2（PARP-2）抑制剂。

  DOI：

  10.1039/c0ob00665c

文献信息

• 5-Substituted isoquinoline derivatives
  申请人：Yamada Rintaro

  公开号：US20050020623A1

  公开（公告）日：2005-01-27

  A compound represented by the following formula (1) or a salt thereof: wherein R 1 represents hydrogen atom, a halogen atom and the like; R 2 represents hydrogen atom, a halogen atom, a C 1-6 alkyl group and the like; and R 3 represents —O—X—C(A 1 )(A 11 )—C(A 2 )(A 2l )—N(A 3l )(A 3 )(X represents propylene group etc., A 11 and A 21 represent hydrogen atom, or a C 1-6 alkyl group, A 31 represents a C 1-6 alkyl group substituted with hydroxyl group, or hydrogen atom, and A 1 , A 2 , and A 3 represent hydrogen atom, a C 1-6 alkyl group and the like) and the like, which has an inhibitory activity on the phosphorylation of myosin regulatory light chain, and is useful for treatment of diseases relating to contraction of various cells and the like.

  由以下公式（1）表示的化合物或其盐： 其中R1代表氢原子、卤素原子等；R2代表氢原子、卤素原子、C1-6烷基团等；R3代表—O—X—C(A1)(A11)—C(A2)(A21)—N(A31)(A3)（X代表丙烯基等，A11和A21代表氢原子或C1-6烷基团，A31代表被羟基取代的C1-6烷基团或氢原子，A1、A2和A3代表氢原子、C1-6烷基团等）等，该化合物对肌球蛋白调节轻链的磷酸化具有抑制作用，并且对涉及各种细胞收缩等的疾病的治疗有益。
• Sulfonamide compound
  申请人：Matsubara Koki

  公开号：US20090048223A1

  公开（公告）日：2009-02-19

  A compound represented by the formula (1) [A represents a nitrogen-containing saturated ring; m represents an integer of 0 to 2; n represents an integer of 1 to 4; G 1 represents hydrogen atom, chlorine atom, hydroxyl group, an alkoxy group, or amino group; G 2 represents a halogen atom, hydroxyl group, cyano group, carboxy group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an amino group, an alkylsulfinyl group, an alkylsulfonyl group, or an aryl group; G 3 represents hydrogen atom, a halogen atom, hydroxyl group, cyano group, carboxy group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an amino group, an alkoxycarbonyl group, an acyl group, an acyloxy group, an alkylsulfinyl group, an alkylsulfonyl group, or an aryl group; Y represents a single bond, or —C(R 3 )(R 4 )— (R 3 and R 4 represent hydrogen atom, or an alkyl group, or alkylene groups which combine together to form a saturated hydrocarbon ring group); G 4 represents hydroxyl group (Y is a single group), or —N(R 1 )(R 2 ) (R 1 and R 2 represent hydrogen atom, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, a saturated heterocyclic group, an alkylsulfonyl group, an acyl group, or an amidino group); G 5 is a substituent on a ring-constituting carbon atom of A, and represents hydrogen atom, fluorine atom, or an alkyl group] or a salt thereof, or a derivative thereof that is a prodrug, which potently inhibits Rho kinase.

  由以下化学式表示的化合物：[A代表含氮饱和环；m表示0到2的整数；n表示1到4的整数；G1代表氢原子、氯原子、羟基、烷氧基或氨基；G2代表卤原子、羟基、氰基、羧基、烷基、烯基、炔基、烷氧基、烷硫基、氨基、烷氧羰基、酰基、乙酰氧基、烷基磺基、烷基磺酰基或芳基；G3代表氢原子、卤原子、羟基、氰基、羧基、烷基、烯基、炔基、烷氧基、烷硫基、氨基、烷氧羰基、酰基、乙酰氧基、烷基磺基、烷基磺酰基或芳基；Y代表单键，或-C(R3)(R4)-（R3和R4代表氢原子、烷基或烷烯基，它们结合在一起形成饱和碳氢环基）；G4代表羟基（Y是单个基），或-N(R1)(R2)（R1和R2代表氢原子、烷基、芳基、烯基、炔基、饱和杂环基、烷基磺酰基、酰基或胺基）；G5是A的环构成碳原子上的取代基，代表氢原子、氟原子或烷基]或其盐、或作为前药的衍生物，其强力抑制Rho激酶。
• SULFONAMIDE COMPOUND
  申请人：Yamada Rintaro

  公开号：US20100093789A1

  公开（公告）日：2010-04-15

  A compound represented by the formula (1) [A represents a nitrogen-containing saturated ring; m represents an integer of 0 to 2; n represents an integer of 1 to 4; G 1 represents hydrogen atom, chlorine atom, hydroxyl group, an alkoxy group, or amino group; G 2 represents a halogen atom, hydroxyl group, cyano group, carboxy group, an alkyl group, an alkenyl group, and the like; G 3 represents hydrogen atom, a halogen atom, hydroxyl group, cyano group, carboxy group, an alkyl group, an alkenyl group, and the like; G 4 represents hydroxyl group, or —N(R 1 )(R 2 ) (R 1 and R 2 represent hydrogen atom, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, or a saturated heterocyclic group); G 5 is a substituent on a ring-constituting carbon atom of A, and represents hydrogen atom, fluorine atom, or an alkyl group] or a salt thereof, or a derivative thereof that is a prodrug, which potently inhibits Rho kinase.

  化合物由以下公式表示(1) [A代表含氮饱和环；m表示0到2的整数；n表示1到4的整数；G1代表氢原子、氯原子、羟基、烷氧基或氨基；G2代表卤原子、羟基、氰基、羧基、烷基、烯基等；G3代表氢原子、卤原子、羟基、氰基、羧基、烷基、烯基等；G4代表羟基，或-N(R1)(R2) (R1和R2代表氢原子、烷基、芳基烷基、烯基、炔基或饱和杂环基)；G5是A的环构成碳原子上的取代基，代表氢原子、氟原子或烷基]或其盐，或其作为前药的衍生物，强力抑制Rho激酶。
• 5-SUBSTITUTED ISOQUINOLINE DERIVATIVE
  申请人：Asahi Kasei Pharma Corporation

  公开号：EP1541559A1

  公开（公告）日：2005-06-15

  A compound represented by the following formula (1) or a salt thereof: wherein R1 represents hydrogen atom, a halogen atom and the like; R2 represents hydrogen atom, a halogen atom, a C1-6 alkyl group and the like; and R3 represents -O-X-C(A1)(A11)-C(A2)(A21)-N(A31)(A3) (X represents propylene group etc., A11 and A21 represent hydrogen atom, or a C1-6 alkyl group, A31 represents a C1-6 alkyl group substituted with hydroxyl group, or hydrogen atom, and A1, A2, and A3 represent hydrogen atom, a C1-6 alkyl group and the like) and the like, which has an inhibitory activity on the phosphorylation of myosin regulatory light chain, and is useful for treatment of diseases relating to contraction of various cells and the like.

  下式（1）所代表的化合物或其盐： 其中 R1 代表氢原子、卤素原子等；R2 代表氢原子、卤素原子、C1-6 烷基等；R3 代表-O-X-C(A1)(A11)-C(A2)(A21)-N(A31)(A3) （X 代表丙烯基等）、A11和A21代表氢原子或C1-6烷基，A31代表被羟基或氢原子取代的C1-6烷基，A1、A2和A3代表氢原子、C1-6烷基等）等，对肌球蛋白调节轻链的磷酸化具有抑制活性，可用于治疗与各种细胞收缩有关的疾病等。
• SULFONAMIDE DERIVATIVE
  申请人：Asahi Kasei Pharma Corporation

  公开号：EP2130828A1

  公开（公告）日：2009-12-09

  A compound represented by the formula (1) [A represents a nitrogen-containing saturated ring; m represents an integer of 0 to 2; n represents an integer of 1 to 4; G1 represents hydrogen atom, chlorine atom, hydroxyl group, an alkoxy group, or amino group; G2 represents a halogen atom, hydroxyl group, cyano group, carboxy group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an amino group, an alkylsulfinyl group, an alkylsulfonyl group, or an aryl group; G3 represents hydrogen atom, a halogen atom, hydroxyl group, cyano group, carboxy group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an amino group, an alkoxycarbonyl group, an acyl group, an acyloxy group, an alkylsulfinyl group, an alkylsulfonyl group, or an aryl group; Y represents a single bond, or -C(R3)(R4)- (R3 and R4 represent hydrogen atom, or an alkyl group, or alkylene groups which combine together to form a saturated hydrocarbon ring group); G4 represents hydroxyl group (Y is a single group), or - N(R1)(R2) (R1 and R2 represent hydrogen atom, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, a saturated heterocyclic group, an alkylsulfonyl group, an acyl group, or an amidino group); G5 is a substituent on a ring-constituting carbon atom of A, and represents hydrogen atom, fluorine atom, or an alkyl group] or a salt thereof, or a derivative thereof that is a prodrug, which potently inhibits Rho kinase.

  由式(1)代表的化合物[A 代表含氮饱和环；m 代表 0 至 2 的整数；n 代表 1 至 4 的整数；G1 代表氢原子、氯原子、羟基、烷氧基或氨基；G2 代表卤素原子、羟基、氰基、羧基、烷基、烯基、炔基、烷氧基、烷硫基、氨基、烷基亚磺酰基、烷基磺酰基或芳基；G3 代表氢原子、卤素原子、羟基、氰基、羧基、烷基、烯基、炔基、烷氧基、烷硫基、氨基、烷氧基羰基、酰基、酰氧基、烷基亚磺酰基、烷基磺酰基或芳基；Y 代表单键，或-C(R3)(R4)-（R3 和 R4 代表氢原子，或烷基，或结合在一起形成饱和烃环基的亚烷基）； G4 代表羟基（Y 为单个基团），或-N(R1)(R2)（R1 和 R2 代表氢原子，或烷基，或芳烷基，或烯基，或炔基，或饱和杂环基，或烷基磺酰基，或酰基，或脒基）；G5 是 A 的成环碳原子上的取代基，代表氢原子、氟原子或烷基]或其盐或其衍生物，它们是原药，能有效抑制 Rho 激酶。