CN109180587A - 一种吡唑类似物的新用途 - Google Patents

一种吡唑类似物的新用途 Download PDF

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Publication number
CN109180587A
CN109180587A CN201811102897.3A CN201811102897A CN109180587A CN 109180587 A CN109180587 A CN 109180587A CN 201811102897 A CN201811102897 A CN 201811102897A CN 109180587 A CN109180587 A CN 109180587A
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Prior art keywords
hydrogen
pyrazole analogs
new application
application
pyrazole
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CN201811102897.3A
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Inventor
徐学涛
吕卉
黄丹颖
张焜
李冬利
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International Healthcare Innovation Institute (jiangmen)
Wuyi University
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International Healthcare Innovation Institute (jiangmen)
Wuyi University
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Priority to CN201811102897.3A priority Critical patent/CN109180587A/zh
Publication of CN109180587A publication Critical patent/CN109180587A/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

本发明公开了一种吡唑类似物的新用途，所述吡唑类似物结构通式如式(Ⅰ)所示：

Description

一种吡唑类似物的新用途
技术领域
本发明涉及医药领域，具体涉及一种一种吡唑类似物的新用途。
技术背景
酪氨酸酶是一种在动植物体内及微生物中广泛存在的含铜离子的氧化还原酶，具有单酚酶和双酚酶的双重特性，是生物体内黑色素合成及色斑产生的关键酶。酪氨酸酶的过度表达会造成黑色素堆积，从而导致多种疾病的发生，如老年斑、雀斑、黄褐斑以及恶性黑色瘤等。酪氨酸酶抑制剂可以抑制黑色素生成，用来预防和治疗色素沉着和黑色素瘤，还可用作防止蔬菜水果褐变的保鲜剂和杀虫剂。因此，其在医药、化妆品、食品工业和农业等领域都有着广阔的应用前景。
发明内容
本发明的目的在于提供一种吡唑类似物在酪氨酸酶抑制剂和美白祛斑添加剂中的应用。
所述吡唑类似物的结构通式如下：
其中：R1，R2，R3可为氢、氟、氯、溴、甲氧基、甲基、腈基或三氟甲基。
具体实施方式
为了更好的说明本发明的目的、技术方案和优点，下面将结合具体实施例对本发明进行说明。
实施例1
本实施例研究本发明所述吡唑类似物在体外抑制酪氨酸酶的作用。
将本发明的吡唑类似物用二甲基亚峰配置成浓度为2mmol/L的母液。将10μL酪氨酸酶(浓度为666.6U/mL)、10μL化合物母液、与130μL磷酸盐缓冲溶液(浓度为50mmol/L)混合后加入50μL L-DOPA(浓度为1mmol/L)，混合均匀后在475nm波长下测定1分钟吸光度的变化。以二甲基亚峰作为空白对照组。抑制活性＝[吸光度(空白)-吸光度(化合物)]/吸光度(空白)×100％。吡唑类似物在终浓度100μmol/L时抑制酪氨酸酶活性如表1所示：
表1吡唑类似物在终浓度100μmol/L时抑制酪氨酸酶活性
化合物编号 R<sub>1</sub> R<sub>2</sub> R<sub>3</sub> R<sub>4</sub> 抑制率(％)
1 氢 氢 氢 氢 14
2 氢 氢 氢 甲基 18
3 甲基 氢 氢 氢 16
4 氢 甲基 氢 氢 25
5 氢 氢 氢 氯 30
6 氯 氢 氢 氢 22
7 氢 氯 氢 氢 17
8 氢 氟 氢 氢 20
9 氢 溴 氢 氢 15
10 氢 甲氧基 氢 氢 21
11 氢 腈基 氢 氢 17
12 氢 三氟甲基 氢 氢 16
13 三氟甲基 氢 三氟甲基 氢 15
14 甲氧基 氢 甲氧基 氢 11
实施例2
本实施例研究本发明化合物5体外抑制酪氨酸酶的半数抑制浓度。
配置不同浓度的化合物5的母液，参照实施例1中的实验方法，测定不同浓度化合物5抑制酪氨酸酶活性，进而可算得半数抑制浓度为605.2μmol/L。

Claims (3)

1.一种吡唑类似物的新用途，其特征在于，所述吡唑类似物具有如下结构通式：
其中：R1，R2，R3，R4可为氢、氟、氯、溴、甲氧基、甲基、腈基或三氟甲基。
2.根据权利要求1所述一种吡唑类似物的新用途，其特征在于，所述新用途为在制备酪氨酸酶抑制剂中的应用。
3.根据权利要求1所述一种吡唑类似物的新用途，其特征在于，所述新用途为在制备美白祛斑添加剂中的应用。
CN201811102897.3A 2018-09-20 2018-09-20 一种吡唑类似物的新用途 Pending CN109180587A (zh)

Priority Applications (1)

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CN201811102897.3A CN109180587A (zh) 2018-09-20 2018-09-20 一种吡唑类似物的新用途

Applications Claiming Priority (1)

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Country Status (1)

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CN (1) CN109180587A (zh)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001064206A2 (en) * 2000-02-29 2001-09-07 Integriderm, Inc. Inhibitors of melanocyte tyrosinase as topical skin lighteners
CN104961735A (zh) * 2015-07-20 2015-10-07 武汉理工大学 吡唑啉衍生物及其作为酪氨酸酶抑制剂的用途
CN107162976A (zh) * 2017-07-07 2017-09-15 五邑大学 一种合成取代的1‑磺酰基‑1h‑吡唑的方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001064206A2 (en) * 2000-02-29 2001-09-07 Integriderm, Inc. Inhibitors of melanocyte tyrosinase as topical skin lighteners
CN104961735A (zh) * 2015-07-20 2015-10-07 武汉理工大学 吡唑啉衍生物及其作为酪氨酸酶抑制剂的用途
CN107162976A (zh) * 2017-07-07 2017-09-15 五邑大学 一种合成取代的1‑磺酰基‑1h‑吡唑的方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BANG-HONG ZHANG等: "Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles", 《CHEM. COMMUN.》 *
PERVAIZ ALI CHANNAR等: "Synthesis of aryl pyrazole via Suzuki coupling reaction, in vitro mushroom tyrosinase enzyme inhibition assay and in silico comparative molecular docking analysis with Kojic acid", 《BIOORGANIC CHEMISTRY》 *
SHRIKANT S. GAWANDE等: "Synthesis of new heterocyclic hybrids based on pyrazole and thiazolidinone scaffolds as potent inhibitors of tyrosinase", 《BIOORGANIC & MEDICINAL CHEMISTRY》 *

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