4-imidazolyl quinoline and quinazoline ketone aromatizing enzyme inhibitors as well as preparation method and medical application thereof

An alkyl, pharmaceutical technology, applied in the field of 4-imidazolyl quinoline and quinazolinone aromatase inhibitors, prevention or treatment of estrogen maintenance diseases

Active Publication Date: 2013-05-22
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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But the therapy is only effective i...

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  • 4-imidazolyl quinoline and quinazoline ketone aromatizing enzyme inhibitors as well as preparation method and medical application thereof
  • 4-imidazolyl quinoline and quinazoline ketone aromatizing enzyme inhibitors as well as preparation method and medical application thereof
  • 4-imidazolyl quinoline and quinazoline ketone aromatizing enzyme inhibitors as well as preparation method and medical application thereof

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specific Embodiment approach

[0051] The specific embodiment (described embodiment is only used to illustrate the present invention, is not used to limit the present invention)

preparation example

[0052] The preparation examples of some compounds are as follows:

[0053] Melting point uses XT4 microscopic melting point measuring instrument; NMR spectrometer is Bruker AV500 type (TMS is internal standard); mass spectrometer is Shimadzu GCMS-QP2010 mass spectrometer or Mariner mass spectrometer; infrared spectrometer is Nicolet Impact410 type (KBr Tablets); the elemental analyzer was Elementar Vario EL III.

[0054] The silica gel used for column chromatography is 100-200 mesh, 200-300 mesh or 300-400 mesh silica gel (Qingdao Ocean Chemical Factory), and the eluent is petroleum ether-ethyl acetate system or chloroform-methanol system. GF for thin layer chromatography (TLC) 254 Thin-layer chromatography plate (Yantai Jiangyou Silica Gel Development Co., Ltd.); TLC development system is petroleum ether-ethyl acetate system or chloroform-methanol system, and a small amount of acetic acid is added if necessary; TLC is performed on a ZF7 type three-purpose ultraviolet analyze...

Embodiment 1

[0057] Preparation of o-aminoacetophenone (1)

[0058] Put 1.52g (9.21mmol) o-nitroacetophenone in the reaction flask, add 100mL THF and 50mL water solution, add 5g (92.1mmol) reduced iron powder, drop in 9 drops of concentrated hydrochloric acid, heat up to 70°C, reflux Reaction 2h. TLC monitors that the reaction is complete, stop heating, cool to room temperature, filter to remove iron powder, distill the filtrate under reduced pressure to remove THF, extract with ethyl acetate, combine organic phases, wash with water, wash with saturated brine, and anhydrous NaSO 4 Dry overnight, and distill to dryness under reduced pressure to obtain about 1.13 g of light yellow oily o-aminoacetophenone (1), with a yield of 91%. ESI-MS: m / z=136[M+H] +

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Abstract

The invention relates to the field of medicinal chemistry and in particular relates to 4-imidazolyl quinoline and quinazoline ketone aromatizing enzyme inhibitors. The invention further discloses a preparation method and pharmacological activity of the inhibitors, a medicinal composition containing the compounds as well as the medical application of the inhibitors, in particular the medical application of the inhibitors in preventing or treating estrogen maintaining diseases such as breast cancers, endometrial cancers, female sexual precocity, gynecomastia and the like.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a series of 4-imidazolylquinoline and quinazolinone aromatase inhibitors. The present invention also discloses their preparation methods and pharmacological activities, pharmaceutical compositions containing these compounds and their medical use, especially as prevention or treatment of estrogen-maintained diseases such as breast cancer, endometrial cancer, precocious puberty, Gynecomastia etc. Background technique [0002] Aromatase (CYP19) is one of the cytochrome P450 enzymes, which can catalyze androstenedione and testosterone to remove the 19th carbon and aromatize the A ring to form estradiol and estrone respectively. Rate-limiting enzyme for estrogen biosynthesis. Studies have shown that aromatase acts on the last step of estrogen biosynthesis, so inhibiting the activity of aromatase will not interfere with the synthesis process of other steroids. Inhibition of aromat...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D239/88A61K31/517A61K31/4709A61P5/30A61P35/00A61P15/14A61P15/00
Inventor 向华劳可静唐智超严明宁珊珊张陆勇尤启冬
Owner CHINA PHARM UNIV
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