6-苄基-2-硫脲嘧啶 | 6336-50-1

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-苄基-2-硫脲嘧啶
• 英文名称: 6-benzyl-2-thiouracil
• 英文别名: Benzylthiouracil；6-benzyl-2-sulfanylpyrimidin-4-ol
• CAS: 6336-50-1
• 化学式: C₁₁H₁₀N₂OS
• mdl: MFCD00023224
• 分子量: 218.279
• InChiKey: PNXBXCRWXNESOV-UHFFFAOYSA-N

物化性质

• 熔点：
  216-219 °C
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090
• 安全说明：
  S22,S24/25
• 储存条件：
  -20°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 4-Benzyl-6-Hydroxy-2-Mercaptopyrimidine
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 218,28 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
4-Benzyl-6-Hydroxy-2-Mercaptopyrimidine
Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
4-Benzyl-6-Hydroxy-2-Mercaptopyrimidine
Xn, R22 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
No data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation rate No data available
i) Flammability (solid, gas) No data available
j) Upper/lower No data available
flammability or
explosive limits
k) Vapour pressure No data available
l) Vapour density No data available
m) Relative density No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition No data available
temperature
q) Decomposition No data available
temperature
r) Viscosity No data available
s) Explosive properties No data available
t) Oxidizing properties No data available
Other safety information
No data available

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SECTION 10: Stability and reactivity
Reactivity
No data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
No data available
Hazardous decomposition products
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
No data available
Skin corrosion/irritation
No data available
Serious eye damage/eye irritation
No data available
Respiratory or skin sensitisation
No data available
Germ cell mutagenicity
No data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
No data available
Specific target organ toxicity - single exposure
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
Additional Information
RTECS: Not available

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SECTION 12: Ecological information
Toxicity
No data available
Persistence and degradability
No data available
Bioaccumulative potential
No data available
Mobility in soil
No data available
Results of PBT and vPvB assessment
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
No data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H302 Harmful if swallowed.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

苄基硫氧嘧啶是一种用于治疗甲亢的活性药物成分。

反应信息

• 作为反应物：
  描述：

  6-苄基-2-硫脲嘧啶 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以88%的产率得到6-benzyl-2-(2-methylbenzylthio)pyrimidin-4(3H)-one
  参考文献：
  名称：

  新型2-芳基烷硫基-4-氨基-6-苄基嘧啶作为有效的HIV-1非核苷逆转录酶抑制剂的合成及生物学评价

  摘要：

  已经设计并合成了新型的2-芳烷硫基-4-氨基-6-苄基嘧啶（3a – i）作为S-1DABO和TMC-125类似物杂化分子，并作为HIV-1 RT的抑制剂进行了合成。结果清楚地表明，嘧啶环的N 3 / C 4位置的变化可能影响N 3 / C 4与Lys101残基之间的氢键强度和数目，这对于抗HIV-1 RT活性是必不可少的。生物活性结果也与对接研究一致。

  DOI：

  10.1016/j.bmcl.2009.04.051
• 作为产物：
  描述：

  5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 6-苄基-2-硫脲嘧啶
  参考文献：
  名称：

  作为有效的 HIV-1 非核苷逆转录酶抑制剂的新型 2-芳基烷硫基-5-碘-6-取代-苄基-嘧啶-4(3H)-one 的合成和生物学评价。

  摘要：

  通过一种有效的方法合成了一系列新的 2-芳基烷硫基-5-碘-6-取代苄基-嘧啶-4(3H)-酮 (S-DABOs) 8a-x。评估了它们对 HIV 病毒的生物活性和 RT 测定。一些化合物，尤其是 8h、8l 和 8n，显示出良好的抗 HIV-1 RT 活性，IC50 值在 0.41 μM 至 0.71 μM 的范围内，远优于奈韦拉平。分子模型研究表明，结合模式会通过在 C-2 侧链上加入氧原子形成额外的氢键而受到影响。生物活性与对接结果一致。

  DOI：

  10.3390/molecules19067104

文献信息

• 5-Iodo-2-arylalkylthio-6-aryl pyrimidin-4(3H)-ones as non-nucleoside anti-HBV agents
  作者：Yu Zhang、Xuefeng Sun、Ningning Fan、Jianxiong Zhao、Jing Tu、Xiangmei Chen、Junyi Liu、Xiaowei Wang

  DOI：10.1039/c5md00181a

  日期：——

  A series of 5-iodo-2-arylalkylthio-6-aryl pyrimidin-4(3H)-ones, which can be considered as S-DABO derivatives, have been synthesized and their antiviral effect on extracellular HBV DNA was evaluated using the HepAD38 cell system. Compounds 6d1 and 6e3 exhibited more potent anti-HBV activity than lamivudine with EC50 values of 0.376 μM and 0.469 μM, respectively. In addition, inhibition of intracellular

  合成了一系列5-碘-2-芳基烷硫基-6-芳基嘧啶-4（3 H）-酮，可以将其视为S-DABO衍生物，并使用HepAD38评估了它们对细胞外HBV DNA的抗病毒作用细胞系统。与拉米夫定相比，化合物6d1和6e3表现出更强的抗HBV活性，EC 50值分别为0.376μM和0.469μM。此外，检查了化合物6d1和6e3对细胞内HBV DNA，pgRNA，HBeAg和HBsAg的抑制作用，以初步推断其作用机理。pgRNA的RT-PCR分析表明，这些新的S-DABO类似物不会干扰HBV转录。TRFIA分析显示化合物6d1和6e3有效减少了HBeAg的分泌。这些结果表明5-碘-2-芳基烷基硫基-6-芳基嘧啶-4（3H）-具有抗HBV能力，可以用作抗HBV感染的潜在药物，并具有低细胞毒性的优点。
• Synthesis and Biological Properties of Novel, Uracil-Containing Histone Deacetylase Inhibitors
  作者：Antonello Mai、Silvio Massa、Dante Rotili、Silvia Simeoni、Rino Ragno、Giorgia Botta、Angela Nebbioso、Marco Miceli、Lucia Altucci、Gerald Brosch

  DOI：10.1021/jm0605536

  日期：2006.10.1

  A novel series of compounds containing a uracil moiety as the connection unit between a phenyl/phenylalkyl portion and a N-hydroxy-polymethylenealkanamide or -methylenecinnamylamide group (uracil-based hydroxamic acids, UBHAs) was tested against maize histone deacetylases (HDACs) and mouse HDAC1. Compounds with a phenyl/benzyl ring at the uracil-C6 position and bearing 4-5 carbon units as well as a

  测试了一系列新的化合物，其中包含尿嘧啶部分作为苯基/苯基烷基部分与N-羟基-聚亚甲基铝酰胺或-亚甲基肉桂酰胺基之间的连接单元（基于尿嘧啶的异羟肟酸，UBHA）对玉米组蛋白脱乙酰基酶（HDACs）和小鼠的抑制作用HDAC1。最有效的抑制剂是在尿嘧啶-C6位置具有苯基/苄基环且带有4-5个碳单元以及间-或对-亚甲基肉桂基部分作为间隔基的化合物。在基于细胞的人类HDAC1和HDAC4分析中，测试的两个UBHA抑制了HDAC1，但没有抑制HDAC4的免疫沉淀活性。在人白血病U937细胞中进行测试时，一些UBHA会导致细胞周期的G1期停滞。此外，1j显示出高抗增殖和剂量依赖性的粒细胞分化特性。
• Desulfurization of 2-Thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with Oxiranes and 2-Haloacetonitriles
  作者：I. A. Novakov、B. S. Orlinson、M. B. Navrotskii

  DOI：10.1007/s11178-005-0211-1

  日期：2005.4

  A procedure was developed for the synthesis of tetrahydropyrimidine-2,4-diones by desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes or 2-haloacetonitriles in polar solvents in the presence of a base.

  一种合成四氢嘧啶-2,4-二酮的方法被开发出来，具体通过在极性溶剂中存在碱的情况下，用环氧烷或2-卤代乙腈对2-噻唑-1,2,3,4-四氢嘧啶-4-酮进行脱硫反应。
• Tetrahydropyrimidine derivatives
  申请人：Shell Research Limited

  公开号：US05332745A1

  公开（公告）日：1994-07-26

  The invention provides a fungicidal composition comprising a carrier and, as active ingredient, certain tetrahydropyrimidine derivatives of the general formula ##STR1## or an acid-addition salt or metal salt complex thereof, in which n is 0, 1, 2 or 3; R represents an optionally substituted alkyl, aryl or aralkyl group; R.sup.1 represents a hydrogen atom or an optionally substituted alkyl or aralkyl group; R.sup.2 represents an optionally substituted aryl group; p is 0 or 1; X represents a group --NR.sup.3 -- or --NR.sup.3 --NR.sup.3 -- where each R.sup.3 independently represents a hydrogen atom or an optionally substituted alkyl, aryl or aralkyl group or R.sup.1 and (X).sub.p --A--R.sup.2 together represent a group --(CR.sup.4 R.sup.5).sub.q --N(A--R.sup.2)-- where q is 2 or 3 and each of R.sup.4 and R.sup.5 is independently selected from a group consisting of hydrogen atoms and optionally substituted alkyl groups; and A represents a group --(CR.sup.6 R.sup.7).sub.m -- where m is 0, 1, 2, 3 or 4 and each of R.sup.6 and R.sup.7 is independently selected from a group consisting of hydrogen atoms and optionally substituted alkyl groups.

  这项发明提供了一种杀真菌组合物，包括载体和作为活性成分的某些四氢吡咯烷衍生物，其通式为##STR1##或其酸加合盐或金属盐络合物，其中n为0、1、2或3；R代表一个可选择的取代烷基、芳基或芳基烷基；R.sup.1代表氢原子或可选择的取代烷基或芳基烷基；R.sup.2代表可选择的取代芳基；p为0或1；X代表一个基团--NR.sup.3--或--NR.sup.3--NR.sup.3--，其中每个R.sup.3独立地代表氢原子或可选择的取代烷基、芳基或芳基烷基，或者R.sup.1和(X).sub.p--A--R.sup.2一起代表一个基团--(CR.sup.4R.sup.5).sub.q--N(A--R.sup.2)--，其中q为2或3，每个R.sup.4和R.sup.5独立地选自由氢原子和可选择的取代烷基；A代表一个基团--(CR.sup.6R.sup.7).sub.m--，其中m为0、1、2、3或4，每个R.sup.6和R.sup.7独立地选自氢原子和可选择的取代烷基。
• Preparation and anti-HIV-1 activity of Thio Analogues of Dichydroalkoxybenzyloxopyrimidines
  作者：Antonello Mai、Marino Artico、Gianluca Sbardella、Silvio Massa、Anna Giulia Loi、Enzo Tramontano、Patrizia Scano、Paolo La Colla

  DOI：10.1021/jm00017a010

  日期：1995.8

  double methyl-substituted series, a more pronounced cytotoxicity was observed and the further introduction of a methyl at the 3'-position in the benzylidene group resulted in total loss of antiviral activity. S-DABOs, namely 2-(alkylthio)-6-benzyl-3,4-dihydro-4-oxopyrimidines, were synthesized by reacting proper methyl (phenylacetyl)acetates or their 2-methyl compounds with thiourea to afford 6-benzyl-4-oxo-1

  二氢烷氧基苄基氧嘧啶（DABOs），一种新型的非核苷类逆转录酶抑制剂的各种硫代类似物，在体外选择性地抑制了HIV-1的繁殖。在C-5 H取代的6-苄基-3,4-二氢-4-氧嘧啶中，在嘧啶环的C-2处引入烷硫基或环烷硫基取代基导致衍生物（S-DABO）最多达到10个-强于烷氧基或环烷氧基的对应物。在2-（烷硫基）-6-苄基尿嘧啶的苄基部分的3'-位处进一步引入甲基，降低了细胞毒性，从而导致更具选择性的化合物。在C-5甲基取代的S-DABO中，许多衍生物显示的EC50值低至0.6 microM，并且在高至300 microM的剂量下没有细胞毒性。在C-5双甲基取代的系列中，观察到更明显的细胞毒性，并且在亚苄基的3'-位处进一步引入甲基导致抗病毒活性完全丧失。S-DABO，即2-（烷硫基）-6-苄基-3,4-二氢-4-氧嘧啶，是通过使适当的（苯基乙酰基）乙酸甲酯或它们的2-甲基化合物与硫脲反应生成6-苄基-4合成的-氧代-1