2,4-二氨基嘧啶-5-腈 | 16462-27-4

• 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: 2,4-二氨基嘧啶-5-腈
• 中文别名: 2,4-二氨基嘧啶-5-甲腈；2,4-二氨基-5-氰基嘧啶
• 英文名称: 2,4-diamino-pyrimidine-5-carbonitrile
• 英文别名: 2,4-diamino-5-pyrimidine carbonitrile；2,4-diaminopyrimidine-5-carbonitrile；2,4-diamino-5-cyanopyrimidine；5-cyano-2,4-diaminopyrimidine；2,4-Diamino-pyrimidin-5-carbonitril；2,4-Diamino-5-cyan-pyrimidin
• CAS: 16462-27-4
• 化学式: C₅H₅N₅
• mdl: MFCD00085600
• 分子量: 135.128
• InChiKey: OYUQCQCQLDTRHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  318 °C (decomp)
• 沸点：
  498.2±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)
• 溶解度：
  DMF（轻微加热）、DMSO（轻微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  Refrigerator

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,4-Diaminopyrimidine-5-carbonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2,4-Diaminopyrimidine-5-carbonitrile
CAS number: 16462-27-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C5H5N5
Molecular weight: 135.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,4-二氨基嘧啶-5-腈 在 甲酸 、 氨 作用下， 以 水 为溶剂， 以78.29%的产率得到2,4-二氨基嘧啶-5-甲醛
  参考文献：
  名称：

  机会病原菌新型二氢叶酸还原酶抑制剂的设计，合成，生物学评价和计算研究

  摘要：

  目前的工作涉及新型，多样的化合物的设计，合成和生物学评估，这些化合物可作为机会微生物中二氢叶酸还原酶（DHFR）的潜在抑制剂。卡氏肺孢子虫（pc），弓形虫（tg）和鸟分枝 杆菌（嘛）。设计了一组14种结构多样的化合物，这些化合物具有DHFR抑制剂的关键药理学特征，远侧大体积取代以及连接远侧部分和2,4-二氨基嘧啶核的不同桥。合成了设计的化合物，并在酶分析中针对pc，tg和ma DHFR进行了评估。大鼠肝脏（rI）DHFR被用作哺乳动物标准品。作为该项目的下一个逻辑步骤，进行了灵活的分子对接研究，以预测这些化合物在pcDHFR活性位点的结合方式，并使用MM-GBSA协议对获得的对接位姿进行后处理，以预测相对结合亲和力。在大多数情况下，预测的结合模式能够使实验结果合理化。特别令人感兴趣的是，对接分数和MM-GBSA预测的ΔG结合能够区分活性化合物和低活性化合物。此外，在IC 50值和MM-GBSA预测的ΔG结合之间获得了0

  DOI：

  10.1016/j.bmc.2010.03.031
• 作为产物：
  描述：

  2-硫乙基-4-氨基-5-氰基嘧啶 在 乙醇 、 氨 作用下， 生成 2,4-二氨基嘧啶-5-腈
  参考文献：
  名称：

  Matsukawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1942, vol. 62, p. 417,443;dtsch.Ref.S.122,125

  摘要：

  DOI：

文献信息

• Design and optimization of N-acylhydrazone pyrimidine derivatives as E. coli PDHc E1 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study
  作者：Haifeng He、Hongying Xia、Qin Xia、Yanliang Ren、Hongwu He

  DOI：10.1016/j.bmc.2017.08.038

  日期：2017.10

  binding site of Escherichia coli (E. coli) pyruvate dehydrogenase multienzyme complex E1 (PDHc E1), a series of novel ‘open-chain’ classes of ThDP analogs A, B, and C with N-acylhydrazone moieties was designed and synthesized to explore their activities against E. coli PHDc E1 in vitro and their inhibitory activity against microbial diseases were further evaluated in vivo. As a result, A1–23 exhibited moderate

  通过靶向硫胺二磷酸（THDP）结合位点的大肠杆菌（大肠杆菌）丙酮酸脱氢酶多酶复合物E1（PDHC E1），一系列的THDP小说“开链”类的类似物甲，乙，和Ç与ñ -设计并合成了酰基to部分，以探讨它们在体外对大肠杆菌PHDc E1的活性，并在体内进一步评价其对微生物疾病的抑制作用。结果，A1 – 23对大肠杆菌PDHc E1表现出了中度到强效的抑制活性（IC 50 = 0.15–23.55μM）。有效的抑制剂A13，A14，A15，C2具有很强的抑制活性，对大肠杆菌PDHc E1的IC 50值为0.60、0.15、0.39和0.34μM，并且在微生物和哺乳动物之间具有良好的酶选择性抑制作用。特别是，最有效的抑制剂A14可以控制99.37％的米地黄单胞菌（Xanthimonas oryzae pv）。Oryzae。此外，化合物A14在大肠杆菌中的结合特征对PDHc E1进行了研究，以通过分子
• Novel dual inhibitors against FP-2 and PfDHFR as potential antimalarial agents: Design, synthesis and biological evaluation
  作者：Wenhua Chen、Xue Yao、Zhenghui Huang、Fei Mao、Longfei Guan、Yun Tang、Hualiang Jiang、Jian Li、Jin Huang、Lubin Jiang、Jin Zhu

  DOI：10.1016/j.cclet.2017.11.041

  日期：2019.1

  Abstract Resistance to malaria parasites has quickly developed to almost all used antimalarial drugs. Cysteine protease falcipain-2 (FP-2) and Plasmodium falciparum dihydrofolate reductase (PfDHFR) have crucial roles, which are absolutely necessary, in the parasite life cycle. In this study, based on the uniform pharmacophores of reported PfDHFR inhibitors and the first-generation dual inhibitors against

  摘要对疟原虫的抗药性已迅速发展到几乎所有使用过的抗疟药。半胱氨酸蛋白酶falcipain-2（FP-2）和恶性疟原虫二氢叶酸还原酶（PfDHFR）在寄生虫的生命周期中具有至关重要的作用，这是绝对必要的。在这项研究中，基于已报道的PfDHFR抑制剂和第一代针对FP-2和PfDHFR的双重抑制剂的统一药效基团，我们通过片段组装鉴定了一系列新型的双重抑制剂。铅优化导致鉴定出14，它显示出对FP-2和PfDHFR酶（IC50 = 6.8±1.8μmol/ L和IC50 = 8.8±0.3μmol/ L）和恶性疟原虫3D7菌株（IC50 = 2.9μmol）的有效抑制作用/ L）。此外，14个对氯喹抗性恶性疟原虫Dd2菌株的增殖表现出更强的抑制作用（IC50 = 1。比乙胺嘧啶（IC50> 10μmol/ L）高1μmol/ L）和14种对两种临床分离株Fab9（IC50 = 2.6μmol/ L）和GB4（IC50
• N-(4-取代苯乙基)乙酰胺类化合物及其用途
  申请人：华东理工大学

  公开号：CN106938997B

  公开（公告）日：2019-10-11

  本发明涉及乙酰胺类化合物及其用途。本发明公开了一类结构新颖的N‑(4‑取代苯乙基)酰胺类化合物。通过体外活性测试实验表明该类化合物对半胱氨酸蛋白酶(FP‑2)和二氢叶酸还原酶(DHFR)具有酶抑制活性。并且经体外杀疟实验结果表明：该类化合物对野生、耐药疟原虫都具有抑制作用。
• 2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 6. A one-step synthesis of new trimethoprim derivatives and activity analysis by molecular modeling
  作者：Alexander Stuart、Thomas Paterson、Barbara Roth、Edward Aig

  DOI：10.1021/jm00359a009

  日期：1983.5

  ines. The use of 1,2,3-trimethoxybenzene in place of a phenol produces 2,4-diamino-5-(2,3,4-trimethoxybenzyl)pyrimidine, a trimethoprim isomer with low antibacterial activity. The use of molecular models of several of the new ortho-substituted derivatives in the active site of dihydrofolate reductase has provided a rational explanation for their activities relative to trimethoprim.

  已经开发出一种新的2，4-二氨基-5-（4-羟基苄基）嘧啶的路线，该路线涉及2，4-二氨基-5-（羟甲基）嘧啶与苯酚在酸性介质中的缩合。苯酚及其2,6-二烷基衍生物的使用仅产生5-（4-羟基苄基）嘧啶。然而，2，6-二甲氧基苯酚产生5-（3-羟基-2，4-二甲氧基苄基）-和5-（4-羟基-3，5-二甲氧基苄基）嘧啶的混合物。酚缩合已用于制备一系列烷基取代的5-（4-羟基苄基）-和5-（4-烷氧基苄基）嘧啶。用1,2,3-三甲氧基苯代替苯酚可产生2,4-二氨基-5-（2,3,4-三甲氧基苄基）嘧啶，这是一种抗菌活性低的甲氧苄啶异构体。
• New [<i>g</i>]-fused [1,2,4]triazolo[1,5-<i>c</i>]pyrimidines: Synthesis of pyrido[3,2-<i>e</i>] and [4,3-<i>e</i>][1,2,4]triazolo[1,5-<i>c</i>]pyrimidine, pyrimido[5,4-<i>e</i>][1,2,4]triazolo[1,5-<i>c</i>]pyrimidine and [1,2,4]triazolo[1,5-<i>c</i>]pteridine derivatives
  作者：Maria Rosaria Del Giudice、Anna Borioni、Carlo Mustazza、Franco Gatta

  DOI：10.1002/jhet.5570310637

  日期：1994.11

  A number of 2-aryl-substituted pyrido[3,2-e] and [4,3-e][1,2,4]triazolo[1,5-c]pyrimidines and [1,2,4]triazolo[1,5-c]pteridines 11,12a,b,e, their corresponding 5-carbonyl derivatives 7,8a,b,e and some pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ones 7,8c,d have been synthesized, according to different pathways. The new tricyclic heterocycles were prepared with the aim of studying their possible

  一些2-芳基取代的吡啶并[3,2- e ]和[4,3- e ] [1,2,4]三唑[1,5- c ]嘧啶和[1,2,4]三唑[ 1,5- c ]蝶啶11,12a，b，e，其相应的5-羰基衍生物7,8a，b，e和一些嘧啶基[5,4- e ] [1,2,4]三唑[1,5] - c ^ ]嘧啶-5-酮7,8c，D已经根据不同的途径合成。制备新的三环杂环是为了研究它们可能的苯并二氮杂receptor受体亲和力。