2,8-二硫基-6-羟基嘌呤 | 15986-32-0

• 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: 2,8-二硫基-6-羟基嘌呤
• 中文别名: 2,5-二氧代己烷二酸二乙酯；2,8-二疏基-6-羟基嘌呤
• 英文名称: 2,8-Dimercapto-6-hydroxypurine
• 英文别名: 2,8-dithio-6-hydroxypurine；2,8-bis(mercapto)-6-hydroxypurine；Purine-6-ol, 2,8-dimercapto-；2,8-bis(sulfanylidene)-7,9-dihydro-3H-purin-6-one
• CAS: 15986-32-0
• 化学式: C₅H₄N₄OS₂
• mdl: MFCD00047144
• 分子量: 200.245
• InChiKey: NDSUZZIWNBVBKW-UHFFFAOYSA-N

物化性质

• 熔点：
  >320℃
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 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：
  129
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• RTECS号：
  UO9050000
• 海关编码：
  2933990090
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38

SDS

Name:	2 8-Dimercapto-6-hydroxypurine Material Safety Data Sheet
Synonym:	None Known
CAS:	15986-32-0

Section 1 - Chemical Product MSDS Name:2 8-Dimercapto-6-hydroxypurine Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15986-32-0	2,8-Dimercapto-6-hydroxypurine	100	240-120-2

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
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. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 15986-32-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: C5H4N4OS2
Molecular Weight: 200.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
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# 15986-32-0: UO9050000 LD50/LC50:
Not available.
Carcinogenicity:
2,8-Dimercapto-6-hydroxypurine - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 15986-32-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15986-32-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15986-32-0 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：

  2,8-二硫基-6-羟基嘌呤 在 吡啶 、 tetraphosphorus decasulfide 作用下， 生成 7,9-二氢-3H-嘌呤-2,6,8-三硫酮
  参考文献：
  名称：

  Potential Purine Antagonists. XX. The Preparation and Reactions of Some Methylthiopurines¹

  摘要：

  DOI：

  10.1021/ja01531a037
• 作为产物：
  描述：

  硫脲 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2,8-二硫基-6-羟基嘌呤
  参考文献：
  名称：

  Johns; Hogan, Journal of Biological Chemistry, 1913, vol. 14, p. 302

  摘要：

  DOI：

文献信息

• Thiopurine Derivative-Induced Fpg/Nei DNA Glycosylase Inhibition: Structural, Dynamic and Functional Insights
  作者：Charlotte Rieux、Stéphane Goffinont、Franck Coste、Zahira Tber、Julien Cros、Vincent Roy、Martine Guérin、Virginie Gaudon、Stéphane Bourg、Artur Biela、Vincent Aucagne、Luigi Agrofoglio、Norbert Garnier、Bertrand Castaing

  DOI：10.3390/ijms21062058

  日期：——

  decipher at the atomic level the mode of action for the best TXn inhibitors on the ZnF-containing enzymes. We discovered an original inhibition mechanism for the ZnLF-containing Fpg/Nei DNA glycosylases by disulfide cyclic trimeric forms of dithiopurines. This work paves the way for the design and synthesis of a new structural class of inhibitors for selective pharmacological targeting of hNeil1 in cancer

  DNA糖基化酶正在成为炎症，癌症和神经退行性疾病中的相关药理靶标。因此，寻找这些酶的抑制剂已成为非常活跃的研究领域。作为先前工作的延续，该工作表明2-硫代黄嘌呤（2TX）是含锌指（ZnF）的Fpg / Nei DNA糖基化酶的不可逆抑制剂，我们设计并合成了2TX衍生物（TXn）的小型文库并进行了评估它们抑制Fpg / Nei酶的能力。在40种化合物中，四种TXn对Fpg的抑制作用优于2TX。出乎意料的是，但非常有趣的是，两种二硫代衍生物更选择性地和有效地抑制了含无锌指（ZnLF）的酶（分别为人和mivirvirus Neil1 DNA糖基化酶hNeil1和MvNei1）。通过结合化学，生物化学，质谱，盲区和柔性对接以及X射线结构分析，我们在Fpg / Nei酶上定位了新的TXn结合位点。这项工作使我们能够在原子水平上破译最佳的TXn抑制剂对含ZnF的酶的作用方式。我们发现二硫代嘌呤的二硫环三聚体形式对含ZnLF的Fpg
• Studies on Condensed Pyrimidine Systems. XXI. The Isolation and Synthesis of 6-Mercapto-2,8-purinediol (6-Thiouric Acid)
  作者：Gertrude B. Elion、Suzanne Mueller、George H. Hitchings

  DOI：10.1021/ja01521a033

  日期：1959.6
• Charge‐Transfer Mechanisms between Gold Clusters
  作者：Viktoria Torma、Olivia Vidoni、Ulrich Simon、Günter Schmid

  DOI：10.1002/ejic.200390143

  日期：2003.3

  AbstractElectron‐transfer processes in complex chemistry are usually described by Taube’s “outer sphere” and “inner sphere” mechanisms. A behaviour related to these electron‐transfer mechanisms in complex chemistry can be observed for charge‐transfer transport between ligand protected Au55 nanoclusters. A linear dependence between cluster‐cluster distance and activation energy for electron transfer is observed if a noncovalent linkage exists; this interaction is independent of the distance in covalently linked clusters. Instead, the activation energy depends on the electronic nature of the linking molecules. The dithiols 1,5‐dithionaphthaline (1), 4,4′‐thiobis(benzenethiol) (2), and 2,8‐dithio‐6‐hydroxypurine (3) have been used as bifunctional covalent linkers either in their monomeric form (2) or, in the presence of air, dimerized via S−S bonds (1, 2, 3), causing an increase in the distance between the clusters and leading to the cluster networks 4−7. Noncovalent cluster networks are formed either by pellets of clusters with monodentate ligands in 8 and 11, linked only by van der Waals forces, or by using bifunctional spacers that interact with the clusters by ion attractions (9, 10). A study of the activation energies clearly indicates that in the case of noncovalently organized nanoparticles only the cluster spacing is of relevance, even if conjugated π‐systems like in 10 are used. This behaviour corresponds to an outer‐sphere mechanism. On the contrary, for covalently linked clusters the distances between them does not play a visible role. The activation energies all lie below those of the noncovalent examples, and a relation between cluster‐cluster distance and activation energy is not obvious. In those cases the relationship suggests an inner‐sphere mechanism where the transport properties of the spacer play a decisive role. These findings possibly help to explain contradictory reports on the conductivity behaviour of organic molecules. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis, spectroscopic characterization and molecular docking study of ethyl 2-(4-(5, 9-dihydro-6-hydroxy-2-mercapto-4H-purin-8-ylthio) thiophen-2-yl)-2-oxoacetate molecule for the chemotherapeutic treatment of breast cancer cells
  作者：Iruthayaraj Ragavan、Chinnaian Vidya、Shajahan Shanavas、Roberto Acevedo、Ponnusamy M. Anbarasan、Anbarasan Manjri、Annamalai Prakasam、Chinnappan Sudhakar、Thangaswamy Selvankumar

  DOI：10.1016/j.chemphys.2019.110596

  日期：2020.2

  We designed, prepared and evaluated a new ligand Ethyl 2-(4-(5, 9-dihydro-6-hydroxy-2-mercapto-4H-purin-8-ylthio) thiophen-2-yl)-2-oxoacetate for anticancer activity against a panel of the human breast cancer cell. The FT-IR and FT-Raman spectroscopies represent one of the most powerful techniques to study chemical bonding and chemistry identify molecular structure. The results of a study on the Geometries, Electrostatic potential energy map and electronic properties of 6HPET were investigated by ab initio and Density Functional Theory (DFT) with B3LYP functional. The Protein-Ligand (6HPET) interaction plays a significant role in structural properties of the designed drug molecule. Molecular docking results were performed by using the FlexX and LeadIT docking software and the binding energies were obtained as scores from -31.976, -30.8060 and -29.2660 kcal/mol. The above-mentioned compounds can be utilized to the breast cancer therapy and it leads a way to create platforms for chemotherapy or hormonal therapy of breast cancer treatments.
• Potential Purine Antagonists. XX. The Preparation and Reactions of Some Methylthiopurines¹
  作者：C. Wayne Noell、Roland K. Robins

  DOI：10.1021/ja01531a037

  日期：1959.11