4-羟基-6-巯基吡唑(3,4-D)嘧啶 | 24521-76-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 4-羟基-6-巯基吡唑(3,4-D)嘧啶
• 中文别名: 4-羟基-6-巯基吡唑并[3,4-D]嘧啶
• 英文名称: 6-thioxo-1,5,6,7-tetrahydropyrazolo<3,4-d>pyrimidin-4-one
• 英文别名: 4-hydroxy-6-mercapto-pyrazolo<3,4-d>pyrimidine；6-thioxo-1(2),5,6,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-4-one；6-thioxo-1,5,6,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-4-one；6-Thioxo-1,5,6,7-tetrahydro-pyrazolo[3,4-d]pyrimidin-4-on；1,5,6,7-tetrahydro-6-thioxo-4H-pyrazolo[3,4-d]pyrimidin-4-one；6-sulfanylidene-1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one
• CAS: 24521-76-4
• 化学式: C₅H₄N₄OS
• mdl: MFCD00022782
• 分子量: 168.179
• InChiKey: SXRSXYWROQWSGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  >310°C
• 密度：
  1.78±0.1 g/cm3(Predicted)
• 溶解度：
  碱性溶液（微溶），DMSO（微溶）
• 稳定性/保质期：
  如果按照规定使用和储存，则不会分解，请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 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：
  102
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933990090
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密的容器中。应储存在阴凉、干燥的地方。

SDS

Name:	4-Hydroxy-6-mercaptopyrazolo[3 4-d]pyrimidine Material Safety Data Sheet
Synonym:
CAS:	24521-76-4

Section 1 - Chemical Product MSDS Name:4-Hydroxy-6-mercaptopyrazolo[3 4-d]pyrimidine Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24521-76-4	4-Hydroxy-6-mercaptopyrazolo[3,4-d]pyr		246-296-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 24521-76-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H4N4OS
Molecular Weight: 168.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24521-76-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hydroxy-6-mercaptopyrazolo[3,4-d]pyrimidine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 24521-76-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 24521-76-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24521-76-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-羟基-6-巯基吡唑(3,4-D)嘧啶 在 sodium hydroxide 、 水 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 生成 N,N-dimethyl-6-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Potential Purine Antagonists. I. Synthesis of Some 4,6-Substituted Pyrazolo [3,4-d] pyrimidines¹

  摘要：

  DOI：

  10.1021/ja01585a023
• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-羟基-6-巯基吡唑(3,4-D)嘧啶
  参考文献：
  名称：

  带有嘧啶并[5,4-b]吲哚和吡唑并[3,4-d]嘧啶基序的双重 Topo II/HDAC 抑制剂的设计、合成和生物学评价

  摘要：

  拓扑异构酶 II (Topo II) 和组蛋白脱乙酰酶 (HDAC) 都是重要的癌症治疗靶点。在这项研究中，设计并合成了两个系列的含有嘧啶并[5,4- b ]吲哚和吡唑并[3,4- d ]嘧啶基序的新型化合物作为双重 Topo II/HDAC 抑制剂。MTT 测定表明，所有化合物均对三种癌细胞系（MGC-803、MCF-7 和 U937）显示出潜在的抗增殖活性，对正常细胞系（3T3）具有低细胞毒性。在酶活性抑制实验中，化合物7d和8d对Topo II和HDAC表现出优异的双重抑制活性。裂解反应测定显示7d是 Topo II 毒物，与对接结果一致。进一步的实验结果表明，化合物7d和8d在MCF-7细胞中可促进细胞凋亡并显着抑制迁移。分子对接显示化合物7d和8d在活性位点结合 Topo II 和 HDAC。分子动力学模拟表明7d可以稳定地结合Topo II和HDAC。

  DOI：

  10.1016/j.ejmech.2023.115303

文献信息

• Design and synthesis of novel heterofused pyrimidine analogues as effective antimicrobial agents
  作者：Balakumar Chandrasekaran、Srinivasulu Cherukupalli、Sivanandhan Karunanidhi、Afsana Kajee、Rajeshwar Reddy Aleti、Nisar Sayyad、Babita Kushwaha、Srinivas Reddy Merugu、Koleka P. Mlisana、Rajshekhar Karpoormath

  DOI：10.1016/j.molstruc.2019.01.105

  日期：2019.5

  Abstract A total of 66 novel heterofused pyrimidine analogues (pyrazolo[3,4-d]pyrimidine (7-43) and pyrido[2,3-d]pyrimidine (51a-l & 52a-h)) were synthesized by employing suitable methods. The desired structures of all the synthesized compounds were confirmed based on FT-IR, 1H NMR, 13C NMR and HRMS experimental data. Further, 19F NMR and 1H-15N HMBC of the representative compound were presented. All

  摘要 采用合适的方法合成了 66 种新型杂稠嘧啶类似物（吡唑并[3,4-d]嘧啶（7-43）和吡啶并[2,3-d]嘧啶（51a-l & 52a-h））。 . 基于 FT-IR、1H NMR、13C NMR 和 HRMS 实验数据确认了所有合成化合物的所需结构。此外，提供了代表性化合物的 19 F NMR和1H-15N HMBC。筛选所有最终化合物的体外抗结核（结核分枝杆菌；H37 Rv）、抗菌（金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌和铜绿假单胞菌）和抗真菌（新型隐球菌、白色念珠菌和 A.尼日尔）活动。化合物 51d、51j、51k、51l 和 51g 对细菌和真菌菌株显示出良好的抗菌和抗真菌活性（MIC = 12.5 μg/ml），
• Synthesis, anticancer evaluation, and molecular docking studies of some novel 4,6-disubstituted pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 (CDK2) inhibitors
  作者：Srinivasulu Cherukupalli、Balakumar Chandrasekaran、Vladimír Kryštof、Rajeshwar Reddy Aleti、Nisar Sayyad、Srinivas Reddy Merugu、Narva Deshwar Kushwaha、Rajshekhar Karpoormath

  DOI：10.1016/j.bioorg.2018.02.030

  日期：2018.9

  A novel series of 4,6-disubstituted pyrazolo[3,4-d]pyrimidines (7–43) bearing various anilines at C-4 position and thiophenethyl or thiopentane moieties at C-6 position have been designed and synthesized by molecular hybridization approach. All the synthesized compounds were evaluated for in vitro CDK2/cyclin E and Abl kinase inhibitory activity as well as anti-proliferative activity against K-562

  一种新型系列的4,6-二取代的吡唑并[3,4的d ]嘧啶（7 - 43）在在C-6位上C-4位和thiophenethyl或thiopentane部分轴承各种苯胺已设计并通过分子杂交的方法合成。对所有合成的化合物进行体外评估CDK2 / cyclin E和Abl激酶的抑制活性以及针对K-562（慢性粒细胞性白血病）和MCF-7（乳腺癌）的抗增殖活性。结构-活性关系（SAR）研究表明，与C-6上的烷基（硫戊烷​​）和C-6上的双取代苯胺相比，C-6上具有噻吩乙基，C-4上具有单取代苯胺的化合物表现出更好的CDK2抑制活性。脚手架的C-4。特别地，在C-4具有2-氯，3-硝基和4-甲硫基苯胺基团的化合物显示出对CDK2的显着的酶抑制活性，其具有数位微摩尔IC 50值。将在硅片分子对接研究表明可能的结合方向和结合能与观察到的SAR和实验结果一致。另外，一些合成的化合物以微摩尔范围的IC 50值显
• Identification of novel, exosite-binding matrix metalloproteinase-13 inhibitor scaffolds
  作者：Joshua Roth、Dmitriy Minond、Etzer Darout、Qin Liu、Janelle Lauer、Peter Hodder、Gregg B. Fields、William R. Roush

  DOI：10.1016/j.bmcl.2011.09.077

  日期：2011.12

  Matrix metalloproteinase-13 (MMP-13) has been implicated as the protease responsible for collagen degradation in cartilage during osteoarthritis (OA). Compounds that inhibit the metalloproteinase at the Zn binding site typically lack specificity among MMP family members. Analogs of the low-micromolar lead MMP-13 inhibitor 4, discovered through high-throughput screening, were synthesized to investigate

  基质金属蛋白酶 13 (MMP-13) 被认为是负责骨关节炎 (OA) 期间软骨中胶原蛋白降解的蛋白酶。在 Zn 结合位点抑制金属蛋白酶的化合物通常在 MMP 家族成员中缺乏特异性。通过高通量筛选发现的低微摩尔先导 MMP-13 抑制剂4 的类似物被合成以研究该抑制剂系列中的结构-活性关系。4 的系统修饰导致 MMP-13 抑制剂20和24的发现，它们比4对其他 MMP 的选择性更强。化合物20作为 MMP-13 抑制剂的效力也大约是原始 HTS 衍生的先导化合物4 的五倍。
• Synthesis and Biological Evaluation of Some Acyclic 4,6-Disubstituted 1<i>H</i>-Pyrazolo[3,4-d]pyrimidine Nucleosides
  作者：O. Moukha-chafiq、M. L. Taha、A. Mouma、H. B. Lazrek、J. J. Vasseur、E. De Clercq

  DOI：10.1081/ncn-120022697

  日期：2003.10

  Abstract The chemical synthesis and biological evaluation of some acyclic α-[6-(1′-carbamoylalkylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]thioalkylamide nucleosides are described.

  摘要描述了一些无环α-[6-（1'-氨基甲酰基烷基硫基）-1H-吡唑并[3,4-d]嘧啶-4-基]硫代烷基酰胺核苷的化学合成和生物学评估。
• Synthesis and biological activity of 6-azacadeguomycin and certain 3,4,6-trisubstituted pyrazolo[3,4-d]pyrimidine ribonucleosides
  作者：Charles R. Petrie、Howard B. Cottam、Patricia A. McKernan、Roland K. Robins、Ganapathi R. Revankar

  DOI：10.1021/jm00146a007

  日期：1985.8

  3-bromo-4(5H)-oxopyrazolo [3,4-d]pyrimidin-6-yl methyl sulfoxide or 6-amino-3-bromopyrazolo [3,4-d]pyrimidin-4(5H)-one, and subsequent ammonolysis, also gave 7a. The structural assignment of 7a was on the basis of spectral studies, as well as its conversion to the reported guanosine analogue 1d. Application of this glycosylation procedure to 6-(methylthio)-4(5H)-oxopyrazolo[3,4-d]pyrimidine-3-carboxamide gave the corresponding

  制备了几种3,4,6-三取代的吡唑并[3,4-d]嘧啶核糖核苷并对其生物学活性进行了测试。在BF3 X OEt2存在下，将3,6-二溴嘌呤醇与1-O-乙酰-2,3,5-三-O-苯甲酰基-D-核呋喃糖进行高温糖基化，然后进行氨解，得到6-氨基-3 -溴-1-β-D-呋喃呋喃糖基吡唑并-[3，4-d]嘧啶-4（5H）-在e上。3-溴-4（5H）-氧杂唑[3,4-d]嘧啶-6-基甲基亚砜或6-氨基-3-溴吡唑[3,4-d]嘧啶-4（5H）-的类似糖基化一，随后进行氨解，也得到7a。7a的结构分配基于光谱研究，以及其转化为已报道的鸟苷类似物1d的基础。该糖基化程序在6-（甲硫基）-4（5H）-氧吡唑并[3，4-d]嘧啶-3-羧酰胺得到相应的N-1糖基衍生物。16a的去硫和脱苯甲酰化提供了到最近报道的3-氨基甲酰基铝嘌呤醇核糖核苷的替代途径，从而证实了16a的结构分配和从其衍生的核苷。氧化16a并随