6-氨基喹唑啉 | 101421-72-1

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-氨基喹唑啉
• 英文名称: quinazolin-6-amine
• 英文别名: 6-amino-quinazoline
• CAS: 101421-72-1
• 化学式: C₈H₇N₃
• mdl: MFCD10697883
• 分子量: 145.164
• InChiKey: XFGPXURFKAUHQR-UHFFFAOYSA-N

物化性质

• 熔点：
  213.5-214 °C (sublm)
• 沸点：
  335.9±15.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 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：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Aminoquinazoline
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: 6-Aminoquinazoline
CAS number: 101421-72-1

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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, refrigerated.
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: C8H7N3
Molecular weight: 145.2

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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：

  6-氨基喹唑啉 在 盐酸 、 sodium azide 、 sodium acetate 、 sodium nitrite 作用下， 生成 6-azidoquinazoline
  参考文献：
  名称：

  6-叠氮喹啉和6-叠氮二嗪的光解环扩展：一些意想不到的氮杂环庚烷开环反应

  摘要：

  6-叠氮喹啉在MeOH-KOMe-二恶烷中的光解产生8,9-二氢-5,7-二甲氧基-5H-嘧啶并[5,4-]氮杂（5），在酸水解时开环反应成嘧啶-甲醛（ 7）。讨论了这种意外的二甲氧基嘧啶基-氮杂a的形成机理，并与先前涉及6-叠氮基-2,3-二氢呋喃基和6-叠氮基-23-二氢噻吩基-[2,3-b]喹啉的类似结果相关联

  DOI：

  10.1016/s0040-4020(01)89775-1
• 作为产物：
  描述：

  N-[4-(乙氧羰基氨基)苯基]氨基甲酸乙酯 在 氢氧化钾 、 三氟乙酸 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 生成 6-氨基喹唑啉
  参考文献：
  名称：

  A microwave improvement in the synthesis of the quinazoline scaffold

  摘要：

  A rapid and efficient microwave-assisted protocol is described that greatly improves a recent synthetic method developed for quinazoline synthesis. The synthetic protocol is based on the use of cycles of microwave irradiation. The optimization process is reported and the experimental results are compared with those of the conventional synthetic route. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.027

文献信息

• Pyrazole compounds
  申请人：——

  公开号：US20030060453A1

  公开（公告）日：2003-03-27

  Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  提供药物组合物和化合物。发明的化合物显示出抗增殖活性，并且可能促进缺乏正常细胞周期和死亡调控的细胞的凋亡。发明的一个实施例提供了化合物与生理可接受载体组合的药物组合物。该药物组合物可用于治疗过度增殖障碍，包括肿瘤生长、淋巴增殖性疾病、血管生成。发明的化合物是取代吡唑和吡唑啉。
• A new access to quinazolines from simple anilines
  作者：Adriana Chilin、Giovanni Marzaro、Samuele Zanatta、Vera Barbieri、Giovanni Pastorini、Paolo Manzini、Adriano Guiotto

  DOI：10.1016/j.tet.2006.09.103

  日期：2006.12

  A new synthetic pathway to quinazolines is described. This new method uses hexamethylenetetramine in TFA and potassium ferricyanide in aqueous ethanolic KOH, starting from simple N-protected anilines. The method affords substituted quinazolines with high selectivities and good yields, reducing reaction-time and work-up operations.

  描述了一种合成喹唑啉的新途径。该新方法从简单的N保护苯胺开始，在TFA中使用六亚甲基四胺，在含水乙醇KOH中使用铁氰化钾。该方法提供了具有高选择性和良好收率的取代的喹唑啉，减少了反应时间和后处理操作。
• [EN] GALACTOSE-LINKED MULTIMERIC GLYCOMIMETIC INHIBITORS OF E-SELECTINS, GALECTIN-3, AND/OR CXCR4 CHEMOKINE RECEPTORS<br/>[FR] INHIBITEURS GLYCOMIMÉTIQUES MULTIMÈRES LIÉS AU GALACTOSE DE SÉLECTINES E, DE GALECTINE-3 ET/OU DE RÉCEPTEURS DE CHIMIOKINE CXCR4
  申请人：GLYCOMIMETICS INC

  公开号：WO2020219417A1

  公开（公告）日：2020-10-29

  Compounds, compositions, and methods for treating and/or preventing at least one disease, disorder, and/or condition associated with E-selectin, galectin-3, and/or CXCR4 chemokine receptor activity are disclosed herein. For example, multimeric glycomimetic inhibitors ofE-selectins, galectin-3, and/or CXCR4 chemokine receptors and their use for treating and/or preventing inflammatory diseases, fibrosis, and cancers are disclosed. Formula (I).

  本文揭示了用于治疗和/或预防与E-选择素、galectin-3和/或CXCR4趋化因子受体活性相关的至少一种疾病、紊乱和/或状况的化合物、组合物和方法。例如，本文揭示了用于治疗和/或预防炎症性疾病、纤维化和癌症的E-选择素、galectin-3和/或CXCR4趋化因子受体的多聚糖类似物抑制剂及其用途。公式（I）。
• Pyrazol-1-yl-propanamides as SARD and Pan-Antagonists for the Treatment of Enzalutamide-Resistant Prostate Cancer
  作者：Yali He、Dong-Jin Hwang、Suriyan Ponnusamy、Thirumagal Thiyagarajan、Michael L. Mohler、Ramesh Narayanan、Duane D. Miller

  DOI：10.1021/acs.jmedchem.0c00943

  日期：2020.11.12

  We report herein the design, synthesis, and pharmacological characterization of a library of novel aryl pyrazol-1-yl-propanamides as selective androgen receptor degraders (SARDs) and pan-antagonists that exert broad-scope AR antagonism. Pharmacological evaluation demonstrated that introducing a pyrazole moiety as the B-ring structural element in the common A-ring–linkage–B-ring nonsteroidal antiandrogens’

  我们在此报告了作为选择性雄激素受体降解剂 (SARDs) 和泛拮抗剂的新型芳基吡唑-1-基-丙酰胺库的设计、合成和药理学表征，它们具有广泛的 AR 拮抗作用。药理学评估表明，在常见的 A 环-连接-B 环非甾体类抗雄激素的一般药效团中引入吡唑部分作为 B 环结构元件，允许开发具有独特 SARD 和泛拮抗剂活性的新小分子支架甚至与我们最近发布的 AF-1 结合 SARD 相比，例如 UT-155 ( 9 ) 和 UT-34 ( 10）。新型 B 环吡唑表现出有效的 AR 拮抗剂活性，包括有希望的分布、代谢和药代动力学特性，以及广谱 AR 拮抗剂特性，包括有效的体内抗肿瘤活性。26a能够对源自恩杂鲁胺抗性 (Enz-R) VCaP 细胞系的异种移植物诱导 80% 的肿瘤生长抑制。这些结果代表了开发用于治疗 Enz-R 前列腺癌的新型 AR 拮抗剂的进展。
• [EN] SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF<br/>[FR] LIGANDS DE SARD - COMPOSÉS DE DÉGRADATION SÉLECTIFS DE RÉCEPTEURS DES ANDROGÈNES - ET MÉTHODES D'UTILISATION
  申请人：UNIV TENNESSEE RES FOUND

  公开号：WO2017214634A1

  公开（公告）日：2017-12-14

  This invention is directed to pyrrole, pyrazole, imidazole, triazole, and morpholine based selective androgen receptor degrader (SARD) compounds including heterocyclic anilide rings and their synthetic precursors, R-isomers, and non-hydroxylated and/or non-chiral propanamides, and pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, triple negative breast cancer, other cancers expressing the androgen receptor, androgenic alopecia or other hyperandrogenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

  该发明涉及吡咯、吡唑、咪唑、三唑和吗啉基选择性雄激素受体降解剂（SARD）化合物，包括含有杂环苯胺环的合成前体、R-异构体以及非羟基化和/或非手性的丙酰胺，以及在治疗前列腺癌、晚期前列腺癌、去势耐药性前列腺癌、三阴性乳腺癌、其他表达雄激素受体的癌症、雄激素性脱发或其他高雄激素皮肤疾病、肯尼迪病、肌萎缩性侧索硬化（ALS）、腹主动脉瘤和子宫肌瘤等方面的制药组合物和用途，以及用于降低受试者中雄激素受体全长（AR-FL）的水平，包括致病性或耐药突变、AR-剪接变体（AR-SV）和AR的致病性多谷氨酸（polyQ）多态性的方法。