N-[(5-isoquinolyl)sulfonyl]-1,4-butylenediamine | 84468-16-6

• 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: N-[(5-isoquinolyl)sulfonyl]-1,4-butylenediamine
• 英文别名: N-(4-aminobutyl)-5-isoquinolinesulfonamide；N-(4-Aminobutyl)isoquinoline-5-sulfonamide
• CAS: 84468-16-6
• 化学式: C₁₃H₁₇N₃O₂S
• 分子量: 279.363
• InChiKey: FHRRATMJUOJBHY-UHFFFAOYSA-N

物化性质

• 沸点：
  498.6±51.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-溴肉桂醛 、 N-[(5-isoquinolyl)sulfonyl]-1,4-butylenediamine 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 以11 %的产率得到(E)-N-(4-{[3-(4-bromophenyl)-2-propen-1-yl]amino}butyl)-5-isoquinolinesulfonamide
  参考文献：
  名称：

  磺胺类：一类抑制动力 I GTP 酶和网格蛋白介导的内吞作用的芳基磺酰胺，在动物模型中具有抗癫痫作用

  摘要：

  我们发现，dansylcadaverine ( 1 ) 是一种已知的网格蛋白介导的内吞作用 (CME) 细胞内抑制剂，可适度抑制 U2OS 细胞中的动力蛋白 I (dynI) GTP 酶活性 (IC 50 45 μM) 和转铁蛋白 (Tfn) 内吞作用 (IC 50 205 μM) ）。合成了一类新型 GTP 竞争性动力抑制剂，Sulfonadyns™。末端肉桂基部分的引入极大地增强了 dynI 抑制。丹酰基和肉桂基部分之间的刚性二胺或酰胺连接不利于 dynI 抑制。体外抑制 dynI 活性的化合物 <10 id=15> 例如类似物33 (( E ) -N- (6-{[(3-(4-溴苯基)-2-丙烯-1-基]氨基}己基) -5-异喹啉磺酰胺)) 和47 个(( E ) -N -(3-{[3-(4-溴苯基)-2-丙烯-1-基]氨基}丙基)-1-萘磺酰胺)异构体，显示出 dyn IC 50 <4

  DOI：

  10.1039/d2md00371f
• 作为产物：
  描述：

  5-异喹啉磺酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 N-[(5-isoquinolyl)sulfonyl]-1,4-butylenediamine
  参考文献：
  名称：

  磺胺类：一类抑制动力 I GTP 酶和网格蛋白介导的内吞作用的芳基磺酰胺，在动物模型中具有抗癫痫作用

  摘要：

  我们发现，dansylcadaverine ( 1 ) 是一种已知的网格蛋白介导的内吞作用 (CME) 细胞内抑制剂，可适度抑制 U2OS 细胞中的动力蛋白 I (dynI) GTP 酶活性 (IC 50 45 μM) 和转铁蛋白 (Tfn) 内吞作用 (IC 50 205 μM) ）。合成了一类新型 GTP 竞争性动力抑制剂，Sulfonadyns™。末端肉桂基部分的引入极大地增强了 dynI 抑制。丹酰基和肉桂基部分之间的刚性二胺或酰胺连接不利于 dynI 抑制。体外抑制 dynI 活性的化合物 <10 id=15> 例如类似物33 (( E ) -N- (6-{[(3-(4-溴苯基)-2-丙烯-1-基]氨基}己基) -5-异喹啉磺酰胺)) 和47 个(( E ) -N -(3-{[3-(4-溴苯基)-2-丙烯-1-基]氨基}丙基)-1-萘磺酰胺)异构体，显示出 dyn IC 50 <4

  DOI：

  10.1039/d2md00371f

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。
• Isoquinolinesulfonyl derivatives and process for the preparation thereof
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04456757A1

  公开（公告）日：1984-06-26

  A 5-isoquinolinesulfonyl derivative of Formula (I): ##STR1## wherein l is zero or one; m and n each is an integer of one to nine; m+n is an integer of at least one; R.sub.1 is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.5-6 cycloalkyl group or an aryl group; or R.sub.2 and R.sub.3 each is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.5-6 cycloalkyl group, an aryl group or an aralkyl group; R.sub.2 and R.sub.3 are C.sub.1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 7-membered heterocyclic ring with the adjacent nitrogen atom; or the ##STR2## group is a ##STR3## group wherein R.sub.4 and R.sub.5 each is a hydrogen atom, a C.sub.1-10 alkyl group, an aryl group or an aralkyl group and R.sub.6 is a hydrogen atom, a C.sub.1-10 alkyl group, and aryl group, an aralkyl group, a benzoyl group, a cinnamyl group, a cinnamoyl group, a furoyl group or a ##STR4## group wherein R.sub.7 is a C.sub.1-8 alkyl group; and the pharmaceutically acceptable salt thereof; and a process for the preparation thereof. The compounds of this invention have a relaxatory action for vascular smooth muscle and are useful as a vasodilator and a hypotensor.

  一种Formula (I)的5-异喹啉磺酰衍生物：其中l为零或一；m和n均为1至9的整数；m+n至少为一个整数；R.sub.1为氢原子，C.sub.1-10烷基，C.sub.5-6环烷基或芳基；或R.sub.2和R.sub.3各自为氢原子，C.sub.1-10烷基，C.sub.5-6环烷基，芳基或芳基烷基；R.sub.2和R.sub.3为C.sub.1-6烷基基团，并直接或通过氧原子连接形成与相邻氮原子共轭的5-至7-成员杂环环；或##STR2##基团为##STR3##基团，其中R.sub.4和R.sub.5各自为氢原子，C.sub.1-10烷基，芳基或芳基烷基，R.sub.6为氢原子，C.sub.1-10烷基，芳基，芳基烷基，苯甲酰基，肉桂基，肉桂酰基，呋喃基或##STR4##基团，其中R.sub.7为C.sub.1-8烷基；以及其药学上可接受的盐；以及其制备方法。该发明的化合物对血管平滑肌具有松弛作用，并可用作血管扩张剂和降压剂。
• Pharmaceutical agent containing Rho kinase inhibitor
  申请人：——

  公开号：US20020032148A1

  公开（公告）日：2002-03-14

  A Rho kinase inhibitor is provided as a novel pharmaceutical agent, particularly as a therapeutic agent of hypertension, a therapeutic agent of angina pectoris, a suppressive agent of cerebrovascular contraction, a therapeutic agent of asthma, a therapeutic agent of peripheral circulation disorder, a prophylactic agent of immature birth, a therapeutic agent of arteriosclerosis, an anti-cancer drug, an anti-inflammatory agent, an immunosuppressant, a therapeutic agent of autoimmune disease, an anti-AIDS drug, a contraceptive, a prophylactic agent of digestive tract infection, a therapeutic agent of osteoporosis, a therapeutic agent of retinopathy and a brain function improving drug. In addition, the Rho kinase inhibitor is provided as a reagent and a diagnostic.

  提供了一种新型药物代理——Rho激酶抑制剂，特别用于治疗高血压、心绞痛、脑血管收缩抑制剂、哮喘、周围循环障碍的治疗剂、早产预防剂、动脉硬化的治疗剂、抗癌药物、抗炎剂、免疫抑制剂、自身免疫疾病的治疗剂、抗艾滋病药物、避孕药、消化道感染预防剂、骨质疏松症的治疗剂、视网膜病的治疗剂和脑功能改善药物。此外，Rho激酶抑制剂还可作为试剂和诊断工具。
• Isoquinolinesulfonyl derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04525589A1

  公开（公告）日：1985-06-25

  A 5-isoquinolinesulfonyl derivative of Formula (I): ##STR1## wherein l is zero or one; m and n each is an integer of one to nine; m+n is an integer of at least one R.sub.1 is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.5-6 cycloalkyl group or an aryl group; or R.sub.2 and R.sub.3 each is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.5-6 cycloalkyl group, an aryl group or an aralkyl group; R.sub.2 and R.sub.3 are C.sub.1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 7-membered heterocyclic ring with the adjacent nitrogen atom; or the ##STR2## group is a ##STR3## group wherein R.sub.4 and R.sub.5 each is a hydrogen atom, a C.sub.1-10 alkyl group, an aryl group or an aralkyl group and R.sub.6 is a hydrogen atom, a C.sub.1-10 alkyl group, an aryl group, an aralkyl group, a benzoyl group, a cinnamyl group, a cinnamoyl group, a furoyl group or a ##STR4## group wherein R.sub.7 is a C.sub.1-8 alkyl group; and the pharmaceutically acceptable salt thereof; and a process for the preparation thereof. The compounds of this invention have a relaxatory action for vascular smooth muscle and are useful as a vasodilator and a hypotensor.

  公式（I）的5-异喹啉磺酰衍生物：##STR1## 其中l为零或一；m和n均为1至9的整数；m+n至少为1的整数；R.sub.1为氢原子，C.sub.1-10烷基，C.sub.5-6环烷基或芳基；或R.sub.2和R.sub.3均为氢原子，C.sub.1-10烷基，C.sub.5-6环烷基，芳基或芳基烷基；R.sub.2和R.sub.3是C.sub.1-6烷基，直接或通过氧原子与相邻的氮原子形成5-至7-成员杂环环；或##STR2##基团是##STR3##基团，其中R.sub.4和R.sub.5均为氢原子，C.sub.1-10烷基，芳基或芳基烷基，R.sub.6为氢原子，C.sub.1-10烷基，芳基，芳基烷基，苯甲酰基，肉桂基，肉桂酰基，呋喃基或##STR4##基团，其中R.sub.7为C.sub.1-8烷基；以及其药学上可接受的盐；以及其制备过程。该发明化合物对血管平滑肌具有松弛作用，可用作扩血管剂和降压剂。
• Isoquinolinesulfonyl derivatives which possess a relaxatory action
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04560755A1

  公开（公告）日：1985-12-24

  A 5-isoquinolinesulfonyl derivative of Formula (I): ##STR1## wherein l is zero or one; m and n each is an integer of one to nine; m+n is an integer of at least one; R.sub.1 is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.5-6 cycloalkyl group or an aryl group; or R.sub.2 and R.sub.3 each is a hydrogen atom, a C.sub.1-10 alkyl group, a C.sub.5-6 cycloalkyl group, an aryl group or an aralkyl group; R.sub.2 and R.sub.3 are C.sub.1-6 alkylene groups and linked directly or through an oxygen atom to form a 5- to 7-membered heterocyclic ring with the adjacent nitrogen atom; or the ##STR2## wherein R.sub.4 and R.sub.5 each is a hydrogen atom, a C.sub.1-10 alkyl group, an aryl group or an aralkyl group and R.sub.6 is a hydrogen atom, a C.sub.1-10 alkyl group, an aryl group, an aralkyl group, a benzoyl group, a cinnamyl group, a cinnamoyl group, a furoyl group or a ##STR3## wherein R.sub.7 is a C.sub.1-8 alkyl group; and the pharmaceutically acceptable salt thereof; and a process for the preparation thereof. The compounds of this invention have a relaxatory action for vascular smooth muscle and are useful as a vasodilator and a hypotensor.

  公式（I）的5-异喹啉磺酰衍生物：##STR1## 其中l为零或一；m和n各为1到9的整数；m+n至少为1的整数；R1为氢原子，C1-10烷基，C5-6环烷基或芳基；或R2和R3各为氢原子，C1-10烷基，C5-6环烷基，芳基或芳基烷基；R2和R3为C1-6烷基，直接或通过氧原子与相邻的氮原子连接，形成5-至7-成员的杂环环与；或##STR2## 其中R4和R5各为氢原子，C1-10烷基，芳基或芳基烷基，R6为氢原子，C1-10烷基，芳基，芳基烷基，苯甲酰基，肉桂基，肉桂酰基，呋喃基或##STR3## 其中R7为C1-8烷基；以及其药学上可接受的盐；以及其制备过程。本发明的化合物具有血管平滑肌松弛作用，可用作血管扩张剂和降压剂。