2-氨基-3-氰基-4,5-二甲基吡咯 | 21392-51-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-氨基-3-氰基-4,5-二甲基吡咯
• 中文别名: 2-氨基-3-氰基-4,5-二甲基-1H-吡咯；2-氨基-3-氰基-4,5-二甲基-1氢-吡咯
• 英文名称: 2-amino-4,5-dimethyl-1H-pyrrole-3-carbonitrile
• 英文别名: 2-amino-4,5-dimethyl-3-pyrrole carbonitrile；2-amino-3-cyano-4,5-dimethylpyrrole；2-Amino-3-cyano-4,5-dimethylpyrrol；2-amino-4,5-dimethyl-pyrrole-3-carbonitrile；2-Amino-3-cyano-4-methyl-5-methylpyrrol；2-Amino-3-cyan-4,5-dimethyl-pyrrol
• CAS: 21392-51-8
• 化学式: C₇H₉N₃
• mdl: MFCD00849263
• 分子量: 135.169
• InChiKey: QZVLATXNNPVXEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  178-181°C
• 沸点：
  366.2±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  UN 3439
• 海关编码：
  2933990090
• 安全说明：
  S26
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-3-cyano-4,5-dimethylpyrrole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-3-cyano-4,5-dimethylpyrrole
CAS number: 21392-51-8

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H9N3
Molecular weight: 135.2

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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-氨基-3-氰基-4,5-二甲基吡咯 在 三氯氧磷 作用下， 反应 8.0h， 生成 4-氯-5,6-二甲基-7h-吡咯并[2,3-d]嘧啶
  参考文献：
  名称：

  新的吡咯并[2,3- d ]嘧啶作为有效的VEGFR-2酪氨酸激酶抑制剂的鉴定：设计，合成，生物学评估和分子模型。

  摘要：

  血管内皮生长因子受体2（VEGFR-2）在癌症血管生成中起着至关重要的作用。在当前的研究中，根据已知II型VEGFR-2抑制剂的结构活性关系（SAR）研究，设计并合成了一系列新型的基于吡咯并[2,3- d ]嘧啶的化合物作为VEGFR-2抑制剂。 。评价了新合成的化合物在体外抑制VEGFR-2激酶的能力。所有测试的化合物均表现出高度有效的剂量相关的VEGFR-2抑制作用，IC 50值在纳摩尔范围内。在这些化合物中，带有联芳基尿素部分（12d和15c）的吡咯并[2,3- d ]嘧啶衍生物表现出IC50个值分别为11.9和13.6 nM。此外，大多数新合成的最终化合物已在60种人类癌细胞系中进行了测试。进行了将这些化合物对接成VEGFR-2的非活性构象，这显示了与FDA批准的VEGFR-2激酶抑制剂相当的结合模式。这些新发现的有效激酶抑制剂可被视为开发新的靶向抗癌剂的潜在候选药物。

  DOI：

  10.1016/j.bioorg.2018.09.001
• 作为产物：
  描述：

  N-(1-甲基-2-氧代丙基)乙酰胺 、 丙二腈 在 sodium hydroxide 作用下， 以 水 为溶剂， 以66%的产率得到2-氨基-3-氰基-4,5-二甲基吡咯
  参考文献：
  名称：

  新的吡咯并[2,3- d ]嘧啶作为有效的VEGFR-2酪氨酸激酶抑制剂的鉴定：设计，合成，生物学评估和分子模型。

  摘要：

  血管内皮生长因子受体2（VEGFR-2）在癌症血管生成中起着至关重要的作用。在当前的研究中，根据已知II型VEGFR-2抑制剂的结构活性关系（SAR）研究，设计并合成了一系列新型的基于吡咯并[2,3- d ]嘧啶的化合物作为VEGFR-2抑制剂。 。评价了新合成的化合物在体外抑制VEGFR-2激酶的能力。所有测试的化合物均表现出高度有效的剂量相关的VEGFR-2抑制作用，IC 50值在纳摩尔范围内。在这些化合物中，带有联芳基尿素部分（12d和15c）的吡咯并[2,3- d ]嘧啶衍生物表现出IC50个值分别为11.9和13.6 nM。此外，大多数新合成的最终化合物已在60种人类癌细胞系中进行了测试。进行了将这些化合物对接成VEGFR-2的非活性构象，这显示了与FDA批准的VEGFR-2激酶抑制剂相当的结合模式。这些新发现的有效激酶抑制剂可被视为开发新的靶向抗癌剂的潜在候选药物。

  DOI：

  10.1016/j.bioorg.2018.09.001

文献信息

• SUBSTITUTED 4-(SELENOPHEN-2(OR-3)-YLAMINO)PYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：KASINA LAILA INNOVA PHARMACEUTICALS PRIVATE LIMITED

  公开号：US20130266563A1

  公开（公告）日：2013-10-10

  Selenophene compounds of formula (I) are described herein. In the compounds of Formula (I), ring A is a 6-membered aromatic fused ring, optionally containing one, two or three nitrogen atoms; a 5-membered heteroaromatic fused ring; or a mono- or bicyclic saturated heterocyclic fused ring having at least one ring member selected from the group consisting of N, O, S, SO and SO 2 ; Y in ring B is nitrogen or substituted carbon; X is NR 6 , O, S, S(O), or S(O) 2 . R 1 , R 2 , R 3 , R 4 , and R 6 are defined in the specification. Selenophene compounds of formula (I) may be used in methods of treating cell proliferative disorders, particularly cancer. Pharmaceutical compositions containing selenophene compounds of formula (I) may be used for treatment, inhibition, or control of cancer.

  Selenophene化合物的化学式（I）在此描述。在化合物的化学式（I）中，环A是一个6元芳香融合环，可选地含有一个、两个或三个氮原子；一个5元杂芳融合环；或者至少有一个环成员选自N、O、S、SO和SO2的单环或双环饱和杂环融合环；环B中的Y是氮或取代碳；X是NR6、O、S、S（O）或S（O）2。R1、R2、R3、R4和R6在规范中有定义。化学式（I）的Selenophene化合物可用于治疗细胞增殖紊乱的方法，特别是癌症。含有化学式（I）的Selenophene化合物的药物组合物可用于治疗、抑制或控制癌症。
• Beiträge zur biologischen Aktivität einer neuen Verbindungsklasse
  作者：Martina Frey、Kurt Eger

  DOI：10.1002/ardp.19923250903

  日期：——

  2‐Aminopyrrol‐3‐carbonitrile 1 reagieren mit Acetylencarbonsäureestern zu den 2‐Amino‐3‐cyano‐dihydroindol‐5‐onen 2 und 3. Die Verbindungen erweisen sich in verschiedenen biologischen Testsystemen als cytotoxisch.

  2-aminopyrrole-3-carbonitriles 1 与乙炔羧酸酯反应形成 2-amino-3-cyano-dihydroindol-5-ones 2 和 3。这些化合物已在各种生物测试系统中显示出细胞毒性。
• Annelated pyrrolo-pyrimidines from amino-cyanopyrroles and BMMAs as leads for new DNA-interactive ring systems
  作者：Antonino Lauria、Marcella Bruno、Patrizia Diana、Paola Barraja、Alessandra Montalbano、Girolamo Cirrincione、Gaetano Dattolo、Anna Maria Almerico

  DOI：10.1016/j.bmc.2004.12.027

  日期：2005.3.1

  The efficient one-pot synthesis of several new tricyclic systems of type 1 and 2, obtained from the reaction of substituted 2-amino-3-cyanopyrroles and 3-amino-4-cyanopyrroles with BMMAs, is reported. The duration and yields of the reaction strongly depend on the reactivity of the starting pyrrole and on the size of the ring to be formed. Mechanist features of the reaction were investigated and proposed

  据报道，从取代的2-氨基-3-氰基吡咯和3-氨基-4-氰基吡咯与BMMAs反应中获得了几种新型的1、2型三环系统的高效一锅合成。反应的持续时间和产率在很大程度上取决于起始吡咯的反应性和要形成的环的大小。通过研究3-氨基吡咯-2，4-二氰基取代的反应性，研究并提出了反应机理。报道的方法代表了将BMMA试剂与吡咯衍生物结合使用的第一个例子，并且可以轻松，通用地进入大量迄今未知的吡咯并嘧啶类化合物，并进一步与不同大小的氮杂环进行了退火。这些新的缩聚杂环具有与DNA相互作用的必要条件。
• Preparation of Novel Pyrrolo[2,3‐<i>b</i>]pyridine Derivatives via a New Concise Synthetic Approach
  作者：Na Guo、Haiyong Jia、Xing You、Du Jiang、Kui Lu、Peng Yu

  DOI：10.1002/bkcs.10212

  日期：2015.4

  The pyrrolo[2,3‐b]pyridine core structure, a bioisostere of quinolones, is found in several molecules that possess important biological activity. We describe here a new, concise, three‐step synthesis of pyrrolo[2,3‐b]pyridines starting from L‐alanine. A series of 4,7‐dihydro‐4‐oxo‐1H‐pyrrolo[2,3‐b]pyridine‐5‐carboxylic acid derivatives, which have not been previously reported, were synthesized using

  在几个具有重要生物活性的分子中发现了吡咯并[2,3- b ]吡啶核心结构，是喹诺酮类的生物等排体。我们在这里描述了一种新的，简洁的，三步合成的从L-丙氨酸开始的吡咯并[2,3- b ]吡啶。使用此方法合成了以前未报道的一系列4,7-二氢-4-氧代-1 H-吡咯并[2,3 - b ]吡啶-5-羧酸衍生物。
• Synthesis of Alkylaminoalkylamides of Substituted 2-Aminopyrroles as Potential Local Anesthetic and Antiarrhythmic Agents II: β-Amines
  作者：J.Walter Sowell、Alan J. Block、Mary Elizabeth Derrick、John J. Freeman、Joseph W. Kosh、Philip F. Mubarak、Paul A. Tenthorey

  DOI：10.1002/jps.2600700519

  日期：1981.5

  The synthesis, local anesthetic and antiarrhythmic properties, and CNS toxicity of 14 2-(3-alkylaminoalkylamido)-pyrroles are described. Most of the compounds exhibited local anesthetic activity by the guinea pig wheal test, with seven showing comparable or greater activity than lidocaine. Most compounds also exhibited antiarrhythmic activity; three compounds had more potent activity than lidocaine

  描述了14个2-（3-烷基氨基烷基酰胺基）-吡咯的合成，局部麻醉和抗心律不齐特性以及CNS毒性。大多数化合物通过豚鼠皮脂试验显示出局部麻醉活性，其中七种显示的活性与利多卡因相当或更高。大多数化合物还表现出抗心律不齐的活性。三种化合物比利多卡因具有更强的活性。所有表现出抗心律不齐活性的化合物也对中枢神经系统有毒。然而，具有比利多卡因更大活性的三种化合物中的两种具有更理想的治疗指标。