5-氨基噻唑 | 17721-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基噻唑
• 中文别名: 2,4-二甲氧基溴苯
• 英文名称: 5-aminothiazole
• 英文别名: 1,3-thiazol-5-amine；thiazol-5-amine；5-Thiazolamine
• CAS: 17721-00-5
• 化学式: C₃H₄N₂S
• 分子量: 100.144
• InChiKey: LKFXYYLRIUSARI-UHFFFAOYSA-N

物化性质

• 沸点：
  239.3±13.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  6
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  -20°C，避光，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Thiazolamine
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: 5-Thiazolamine
CAS number: 17721-00-5

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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: C3H4N2S
Molecular weight: 100.1

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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, sulfur 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：

  5-氨基噻唑 、 羟甲香豆素 在 硫酸 、 溶剂黄146 、 sodium nitrite 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.5h， 以72%的产率得到7-hydroxy-4-methyl-6-(thiazol-5-yldiazenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Amjad, Rana; Munawar, Munawar Ali; Khan, Shahid Rehman, Pakistan Journal of Scientific and Industrial Research, 2009, vol. 52, # 3, p. 117 - 121

  摘要：

  DOI：
• 作为产物：
  描述：

  噻唑-5-甲酸 在 叠氮磷酸二苯酯 、 盐酸 作用下， 以 2-甲基-2-丁醇 、 三乙胺 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 5-氨基噻唑
  参考文献：
  名称：

  Pyridyl and thiazolyl bisamide CSF-1R inhibitors for the treatment of cancer

  摘要：

  The bisamide class of kinase inhibitors was identified as being active against CSF-1R. The synthesis and SAR of pyridyl and thiazolyl bisamides is reported, along with the pharmacokinetic properties and in vivo activity of selected examples. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.093

文献信息

• NITROGEN-CONTAINING HETEROCYCLIC COMPOUND OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20150322063A1

  公开（公告）日：2015-11-12

  A compound represented by Formula [1] (in the formula, Z 1 represents N, CH, or the like; X 1 represents NH or the like; R 1 represents a heteroaryl group or the like; each of R 2 , R 3 , and R 4 represents a hydrogen atom, a halogen atom, an alkoxy group, or the like; and R 5 represents a heteroaryl group or the like) or salt thereof.

  由式[1]表示的化合物（在该式中，Z表示N、CH或类似物；X表示NH或类似物；R表示杂环烷基或类似物；R2、R3和R4中的每一个表示氢原子、卤原子、烷氧基或类似物；R5表示杂环烷基或类似物）或其盐。
• Identification and Optimization of the First Highly Selective GLUT1 Inhibitor BAY-876
  作者：Holger Siebeneicher、Arwed Cleve、Hartmut Rehwinkel、Roland Neuhaus、Iring Heisler、Thomas Müller、Marcus Bauser、Bernd Buchmann

  DOI：10.1002/cmdc.201600276

  日期：2016.10.19

  these transporters should not be addressed by such an inhibitor. A high-throughput screen against a library of ∼3 million compounds was performed to find a small molecule with this challenging potency and selectivity profile. The N-(1H-pyrazol-4-yl)quinoline-4-carboxamides were identified as an excellent starting point for further compound optimization. After extensive structure-activity relationship explorations

  尽管众所周知的事实是，即使在正常的氧气供应条件下，促进性葡萄糖转运蛋白GLUT1仍是保证许多肿瘤实体葡萄糖消耗增加的关键因素之一（被称为Warburg效应），但仅进行了很少的努力寻找一种GLUT1选择性小分子抑制剂。由于GLUT1家族的其他转运蛋白都参与关键过程，因此此类抑制剂不应解决这些转运蛋白。针对约300万种化合物的库进行了高通量筛选，以发现具有这种具有挑战性的效能和选择性的小分子。N-（1H-吡唑-4-基）喹啉-4-羧酰胺被确定为进一步优化化合物的理想起点。经过广泛的构效关系探索后，获得了对GLUT2，GLUT3和GLUT4的选择性因子> 100的个位数纳摩尔抑制剂。最有前途的化合物BAY-876 [N4- [1-（4-氰基苄基）-5-甲基-3-（三氟甲基）-1H-吡唑-4-基] -7-氟喹啉-2,4-二甲酰胺]在体外具有良好的代谢稳定性，在体内具有较高的口服生物利用度。
• Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive N-alkylation of secondary amines with ketones through an alternative pathway
  作者：Onkar S. Nayal、Maheshwar S. Thakur、Vinod Bhatt、Manoranjan Kumar、Neeraj Kumar、Bikram Singh、Upendra Sharma

  DOI：10.1039/c6cc04381j

  日期：——

  We report herein a highly efficient, tin(II)/PMHS catalyzed reductive N-alkylation of arylamines with ketones affording tertiary arylamines. Very wide substrate scope was observed for current catalytic method as all six...

  我们在此报告了一种高效的锡（II）/ PMHS催化的芳基胺与酮的还原性N-烷基化反应，提供了叔芳基胺。当前的催化方法观察到非常宽的底物范围，因为所有六个...
• Structure‐Based Design, Synthesis, and Biological Evaluation of Imidazo[4,5‐ <i>b</i> ]Pyridin‐2‐one‐Based p38 MAP Kinase Inhibitors: Part 2
  作者：Akira Kaieda、Masashi Takahashi、Hiromi Fukuda、Rei Okamoto、Shinji Morimoto、Masayuki Gotoh、Takahiro Miyazaki、Yuri Hori、Satoko Unno、Tomohiro Kawamoto、Toshimasa Tanaka、Sachiko Itono、Terufumi Takagi、Hiroshi Sugimoto、Kengo Okada、Weston Lane、Bi‐Ching Sang、Kumar Saikatendu、Shinichiro Matsunaga、Seiji Miwatashi

  DOI：10.1002/cmdc.201900373

  日期：2019.12.17

  yl-1H-pyrazol-3-yl)benzamide (25) exhibited potent p38 inhibition, superior suppression of TNF-α production in hWB cells, and also significant in vivo efficacy in a rat model of collagen-induced arthritis (CIA). In this paper, we report the discovery of potent, selective, and orally bioavailable imidazo[4,5-b]pyridin-2-one-based p38 MAP kinase inhibitors.

  我们使用基于结构的设计策略，从铅化合物3-（butan-2-yl）-6-（2,4-difluoroanilino）-1， 3-二氢-2H-咪唑并[4，5-b]吡啶-2-酮（1）。为了增强1在人全血（hWB）细胞测定中对肿瘤坏死因子-α（TNF-α）产生的抑制活性，我们设计并合成了其中咪唑并[4,5-b] pyridin-2的杂化化合物。 -一个核心与对甲基苯甲酰胺片段成功连接。在所评估的化合物中，3-（3-叔丁基-2-氧代-2,3-二氢-1H-咪唑并[4,5-b]吡啶-6-基）-4-甲基-N-（1-甲基-1H-吡唑-3-基）苯甲酰胺（25）在hWB细胞中显示出有效的p38抑制作用，TNF-α产生的优异抑制作用，并且在胶原诱导的关节炎（CIA）大鼠模型中也具有显着的体内功效。
• Discovery of potent, orally bioavailable ERK1/2 inhibitors with isoindolin-1-one structure by structure-based drug design
  作者：Dezhong Ji、Lingzhi Zhang、Qihua Zhu、Ying Bai、Yaoyao Wu、Yungen Xu

  DOI：10.1016/j.ejmech.2018.12.040

  日期：2019.2

  therapy. Despite the successful development of BRAF and MEK inhibitors in clinic treatment, resistance often appears to re-enhance ERK1/2 signaling. Inspired by the central role of the ERK1/2 signaling cascade in cancer, we describe the scaffold-hopping generation of a series of isoindolin-1-one ERK1/2 inhibitors. Our new compounds could inhibit proliferation of KRAS and BRAF mutant cells lines at low

  在许多肿瘤中经常观察到MAPK（RAS / RAF / MEK / ERK）途径的组成性激活，因此已成为癌症治疗的有趣治疗靶标。尽管在临床治疗中成功开发了BRAF和MEK抑制剂，但耐药性通常似乎可以重新增强ERK1 / 2信号传导。受ERK1 / 2信号级联在癌症中的核心作用的启发，我们描述了一系列isoindolin-1-one ERK1 / 2抑制剂的骨架跳跃产生。我们的新化合物可以在低纳摩尔浓度下抑制KRAS和BRAF突变细胞系的增殖。化合物22a具有可接受的药代动力学特征，并且在HCT-116异种移植模型中显示出可观的体内抗肿瘤功效，为进一步优化临床ERK1 / 2抑制剂提供了有希望的基础。