吲哚洛尔的合成及结构分析
|
摘要
4-羟基吲哚、环氧氯丙烷在氢氧化钠的乙醇溶液中反应生成中间体1-(1H-吲哚-4-氧基)-3-氯-2-丙醇,然后中间体与异丙胺反应,合成出了目标产物吲哚洛尔{1-(1H-吲哚-4-氧基)-3-[(1-甲基乙基)氨基]-2-丙醇}。通过~1H NMR、~(13)C NMR、IR对合成的吲哚洛尔进行表征,结果表明与理论结构一致。
The intermediate 1-(1 H-indole-4-oxy)-3-chloro-2-propanol was formed by the reaction of 4-hydroxyindole and epichlorohydrin in the alcohol solution of sodium hydroxide,and then the intermediate reacted with isopropylamine to synthesis indololol(1-(1 H-indole-4-oxy)-3-[(1-methyl ethyl) amino]-2-propanol.The indolol was characterized by ~1H NMR,~(13)C NMR,IR,and the results showed that it was consistent with the theoretical structure.
The intermediate 1-(1 H-indole-4-oxy)-3-chloro-2-propanol was formed by the reaction of 4-hydroxyindole and epichlorohydrin in the alcohol solution of sodium hydroxide,and then the intermediate reacted with isopropylamine to synthesis indololol(1-(1 H-indole-4-oxy)-3-[(1-methyl ethyl) amino]-2-propanol.The indolol was characterized by ~1H NMR,~(13)C NMR,IR,and the results showed that it was consistent with the theoretical structure.
引文
[1] 陈修,陈维洲,曾贵云.心血管药理学:第2版[M].北京:人民卫生出版社,1997:69-71.
[2] MAGDALENA O,BARBARA M,PIOTR K.Spectroscopic analysis of pindolol irradiated in the solid state[J].Open Chemistry,2013,12(1):60-66.
[3] NAUTIYAL KATHERINE M,TANAKA KENJI F,BARR MARY M,et al.Distinct circuits underlie the effects of 5-HT1B receptors on aggression and impulsivity[J].Neuron,2015,86(3):13-26.
[4] 马养民,刘斌.吲哚二酮哌嗪类化合物的合成研究进展[J].有机化学,2010,30(11):1624-1639.
[5] REGIS B,PIERRE T,BEMARD D,et al.Effect of pindolol on onset of action of paroxetine in the treatment of major depression[ J].Am J Psychiatry,1998,155(10):1346-1351.
[6] 张文会,王丹丹,刘欢欢,等.新型六氢吡啶-2,3-并吲哚化合物的合成及其抗肿瘤活性[J].合成化学,2016,24(5):380-383.
[7] SEAN S,MICHELE P.Pindolol augmentation of selective serotonin reuptake inhibitors and clomipramine for the treatment of obsessive-compulsive disorder:A meta-analysis[J].Journal of Pharmacology and Pharmacotherapeutics,2015,6(1):36-38.
[8] 王德刚,李新胜.吲哚洛尔对帕罗西汀抑郁症显效时间的影响[J].医药导报,2001,20(8):493-494.
[9] 张有志,李云峰,陈爽,等.吲哚洛尔增强帕罗西汀对小鼠的抗抑郁作用[J].军事医学科学院院刊,2006,30(6):596-597.
[10] 施健美,黄睿,左虎进,等.5-{4-[4-(5-氰基-3-吲哚基)丁基]哌嗪基}苯并呋喃-2-甲酸合成方法的改进[J].高校化学工程学报,2015(1):159-163.
[11] 刘金强,钱超,陈新志,等.吲哚-2-甲酸和(S)-吲哚啉-2-甲酸的合成和相互转化研究进展[J].有机化学,2011,31(5):634-645.
[12] 陈永诚,解正峰.吲哚与亚胺的Friedel-Crafts反应的研究进展[J].有机化学,2012,32(3):462-471.
[2] MAGDALENA O,BARBARA M,PIOTR K.Spectroscopic analysis of pindolol irradiated in the solid state[J].Open Chemistry,2013,12(1):60-66.
[3] NAUTIYAL KATHERINE M,TANAKA KENJI F,BARR MARY M,et al.Distinct circuits underlie the effects of 5-HT1B receptors on aggression and impulsivity[J].Neuron,2015,86(3):13-26.
[4] 马养民,刘斌.吲哚二酮哌嗪类化合物的合成研究进展[J].有机化学,2010,30(11):1624-1639.
[5] REGIS B,PIERRE T,BEMARD D,et al.Effect of pindolol on onset of action of paroxetine in the treatment of major depression[ J].Am J Psychiatry,1998,155(10):1346-1351.
[6] 张文会,王丹丹,刘欢欢,等.新型六氢吡啶-2,3-并吲哚化合物的合成及其抗肿瘤活性[J].合成化学,2016,24(5):380-383.
[7] SEAN S,MICHELE P.Pindolol augmentation of selective serotonin reuptake inhibitors and clomipramine for the treatment of obsessive-compulsive disorder:A meta-analysis[J].Journal of Pharmacology and Pharmacotherapeutics,2015,6(1):36-38.
[8] 王德刚,李新胜.吲哚洛尔对帕罗西汀抑郁症显效时间的影响[J].医药导报,2001,20(8):493-494.
[9] 张有志,李云峰,陈爽,等.吲哚洛尔增强帕罗西汀对小鼠的抗抑郁作用[J].军事医学科学院院刊,2006,30(6):596-597.
[10] 施健美,黄睿,左虎进,等.5-{4-[4-(5-氰基-3-吲哚基)丁基]哌嗪基}苯并呋喃-2-甲酸合成方法的改进[J].高校化学工程学报,2015(1):159-163.
[11] 刘金强,钱超,陈新志,等.吲哚-2-甲酸和(S)-吲哚啉-2-甲酸的合成和相互转化研究进展[J].有机化学,2011,31(5):634-645.
[12] 陈永诚,解正峰.吲哚与亚胺的Friedel-Crafts反应的研究进展[J].有机化学,2012,32(3):462-471.