3-脱氧胞苷 | 7057-33-2

• 物质功能分类: 生物化工 - 核苷类药物 - 脱氧核苷酸及其类似物
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 3-脱氧胞苷
• 中文别名: 3'-脱氧胞苷
• 英文名称: 3'-deoxycytidine
• 英文别名: 4-amino-1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 7057-33-2
• 化学式: C₉H₁₃N₃O₄
• mdl: MFCD00079144
• 分子量: 227.22
• InChiKey: ZHHOTKZTEUZTHX-SHYZEUOFSA-N

物化性质

• 熔点：
  230-232 °C
• 沸点：
  497.6±55.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  29389090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: 3′-Deoxycytidine
Product name
CAS-No. : 7057-33-2
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C9H13N3O4
Molecular Weight : 227,22 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
Most important symptoms and effects, both acute and delayed
Deoxycytidine has been found to be markedly less toxic than its dideoxy counterpart, dideoxycytidine.
When used in conjunction with some anti-viral chemical therapies, deoxycytidine has been found to
diminish some of the toxic side effects associated with chemotherapy.
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
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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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) Autoignition 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
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
no data available
Hazardous decomposition products
Other decomposition products - no data available

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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 sensitization
no data available
Germ cell mutagenicity
Genotoxicity in vitro - mouse - fibroblast
DNA inhibition
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
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes
May cause eye irritation.
Signs and Symptoms of Exposure
Deoxycytidine has been found to be markedly less toxic than its dideoxy counterpart, dideoxycytidine.
When used in conjunction with some anti-viral chemical therapies, deoxycytidine has been found to
diminish some of the toxic side effects associated with chemotherapy.
Additional Information
RTECS: HA3830000

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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
no data available
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.
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

4-氨基-1-((2R,3R,5S)-3-羟基-5-(羟甲基)四氢呋喃-2-基)嘧啶-2(1H)-酮（与3'-脱氧胞苷结合）是一种嘌呤核苷类似物。这类化合物具有广泛的抗肿瘤活性，尤其针对惰性淋巴系统恶性肿瘤。其抗癌机制主要依赖于抑制DNA合成和诱导细胞凋亡等过程。

反应信息

• 作为反应物：
  描述：

  3-脱氧胞苷 在 tetrafluoroboric acid 、 1A and BM-11 cells 、 E_. coli BMT-4D 、 氢氟酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 27.0h， 生成 2-氟-3-脱氧腺苷酸
  参考文献：
  名称：

  3-脱氧-β-D-呋喃核糖嘌呤的化学酶合成

  摘要：

  9-(3-Deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine (6) 通过 2,6-diaminopurine (2) 与 3'-deoxycytidine (1) 作为供体的酶促转糖基化合成3-脱氧-D-赤型呋喃糖部分。这种转化包括 i) 在全细胞 (E.coli BM-11) 胞苷脱氨酶 (CDase) 的作用下 1 到 3'-脱氧尿苷 (3) 的脱氨基作用，ii) 尿苷磷酸化酶 (UPase) 对 3 的磷酸分解，从而产生导致形成尿嘧啶 (4) 和 3-deoxy-α-D-erythro-pentofuranose-1-O-phosphate (5)，以及 iii) 后者与 2 在全细胞催化下偶联（大肠杆菌 BMT- 4D/1A) 嘌呤核苷磷酸化酶 (PNPase)。腺苷脱氨酶 (ADase) 对 6 进行脱氨基作用得到 3'-脱氧鸟苷

  DOI：

  10.1002/1522-2675(200207)85:7<1893::aid-hlca1893>3.0.co;2-p
• 作为产物：
  描述：

  胞苷 在 phosphinic acid 、 copper(II) sulfate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 23.33h， 生成 3-脱氧胞苷
  参考文献：
  名称：

  一种3’-脱氧尿苷的制备方法

  摘要：

  本发明涉及药物合成领域，具体是一种3’‑脱氧尿苷的制备方法，以化合物3为原料，先经乙酸酐保护氨基得到化合物4，再在乙酰溴作用下得到化合物5，经过次磷酸盐体系还原得到化合物6；在高压水蒸气与有机溶剂的作用下脱去脱乙酰氨基得化合物8或N‑乙酰基得化合物7，最后脱去全部乙酰基得到3’‑脱氧尿苷和3’‑脱氧胞苷的混合物，分离纯化分别得到3’‑脱氧尿苷和3’‑脱氧胞苷晶体；也可以由化合物6直接脱去全部乙酰基得到3’‑脱氧胞苷。本发明采用易得的天然产物为起始原料，操作简单，纯化方便，极易工业化大规模生产。

  公开号：

  CN107033205B

文献信息

• [EN] COMPOSITIONS AND METHODS FOR SYNTHESIS OF PHOSPHORYLATED MOLECULES<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE DE MOLÉCULES PHOSPHORYLÉES
  申请人：UNIV CALIFORNIA

  公开号：WO2019195494A1

  公开（公告）日：2019-10-10

  The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

  这项发明提供了合成磷酸化有机化合物的组合物和方法，包括核苷三磷酸。
• Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase
  申请人：——

  公开号：US20020147160A1

  公开（公告）日：2002-10-10

  The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

  本发明提供了核苷化合物及其某些衍生物，这些衍生物是RNA依赖性RNA病毒聚合酶的抑制剂。这些化合物是RNA依赖性RNA病毒复制的抑制剂，可用于治疗RNA依赖性RNA病毒感染。它们特别适用于作为丙型肝炎病毒（HCV）NS5B聚合酶的抑制剂，作为HCV复制的抑制剂，以及/或用于治疗丙型肝炎感染。本发明还描述了包含这种核苷化合物的药物组合物，单独使用或与其他对RNA依赖性RNA病毒感染，特别是HCV感染有效的制剂组合使用。还公开了使用本发明的核苷化合物抑制RNA依赖性RNA聚合酶、抑制RNA依赖性RNA病毒复制和/或治疗RNA依赖性RNA病毒感染的方法。
• Nucleotide mimics and their prodrugs
  申请人：——

  公开号：US20040059104A1

  公开（公告）日：2004-03-25

  The present invention relates to nucleoside diphosphate mimics and nucleoside triphosphate mimics, which contain diphosphate or triphosphate moiety mimics and optionally sugar-modifications and/or base-modifications. The nucleotide mimics of the present invention, in a form of a pharmaceutically acceptable salt, a pharmaceutically acceptable prodrug, or a pharmaceutical formulation, are useful as antiviral, antimicrobial, and anticancer agents. The present invention provides a method for the treatment of viral infections, microbial infections, and proliferative disorders. The present invention also relates to pharmaceutical compositions comprising the compounds of the present invention optionally in combination with other pharmaceutically active agents.

  本发明涉及核苷二磷酸模拟物和核苷三磷酸模拟物，其中包含二磷酸或三磷酸基团模拟物，以及可选的糖修饰和/或碱基修饰。本发明的核苷酸模拟物，以药学上可接受的盐、药学上可接受的前药或药物配方的形式，可用作抗病毒、抗微生物和抗癌剂。本发明提供了一种治疗病毒感染、微生物感染和增生性疾病的方法。本发明还涉及包含本发明化合物的药物组合物，可选地与其他药理活性剂结合。
• Oligonucleotides having modified nucleoside units
  申请人：——

  公开号：US20040014957A1

  公开（公告）日：2004-01-22

  Disclosed are oligonucleotides and oligonucleosides that include one or more modified nucleoside units. The oligonucleotides and oligonucleosides are particularly useful as antisense agents, ribozymes, aptamer, siRNA agents, probes and primers or, when hybridized to an RNA, as a substrate for RNA cleaving enzymes including RNase H and dsRNase.

  披露的是包括一个或多个修饰核苷单元的寡核苷酸和寡核苷糖。这些寡核苷酸和寡核苷糖特别适用于作为反义剂、核酶、适配体、siRNA试剂、探针和引物，或者当它们与RNA杂交时，作为包括RNase H和dsRNase的RNA切割酶的底物。
• Synthesis and anticancer activity of various 3'-deoxy pyrimidine nucleoside analogs, and crystal structure of 1-(3-deoxy-.beta.-D-threo-pentofuranosyl)cytosine
  作者：Tai Shun Lin、Jing Hua Yang、Mao Chin Liu、Zhi Yi Shen、Yung Chi Cheng、William H. Prusoff、George I. Birnbaum、Jerzy Giziewicz、Ismail Ghazzouli

  DOI：10.1021/jm00106a034

  日期：1991.2

  Various 3'-deoxy pyrimidine nucleoside analogues have been synthesized for evaluation as potential anticancer and antiviral agents. Among these compounds, 1-(3-deoxy-beta-D-threo-pentofuranosyl)cytosine (10, 3'-deoxy-ara-C) and 3'-deoxycytidine (22) had significant anticancer activity against CCRF-CEM, L1210, P388, and S-180 cancer cell lines in vitro, producing ED50 values of 2, 10, 5, and 34 microM

  已经合成了多种3'-脱氧嘧啶核苷类似物，以评估其作为潜在的抗癌和抗病毒剂。在这些化合物中，1-（3-脱氧-β-D-苏-戊呋喃糖基）胞嘧啶（10，3'-脱氧-ara-C）和3'-脱氧胞苷（22）对CCRF-CEM具有显着的抗癌活性，L1210 ，P388和S-180癌细胞系在体外产生的3'-deoxy-ara-C ED50值分别为2、10、5和34 microM（10）；对于3'-脱氧胞苷（22），分别为25、5、2.5和15 microM。因此，对于CCRF-CEM细胞，3'-脱氧-ara-C（10）的活性是3'-脱氧胞苷（22）的12.5倍。证明了3'-脱氧-ara-C（10）的2'-O-乙酰基，5'-O-乙酰基和2'，5'-二-O-乙酰基衍生物，化合物34、31和30抗癌活性与3'相同 -针对CCRF-CEM，L1210，P388和S-180细胞的-deoxy-ara-C（10）。5'