5-(4-甲氧基苯基)-4H-1,2,4-三唑-3-胺 | 54464-14-1

• 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-(4-甲氧基苯基)-4H-1,2,4-三唑-3-胺
• 中文别名: 5-(4-甲氧苯基)-4H-1,2,4-3-氨基-1,2,4-三氮唑；5-(4-甲氧基苯)-4H-1,2,4-三唑-3-胺0.1H2O；[5-(4-甲氧苯基)-1H-1,2,4-三唑-3-基]胺；5-(4-甲氧苯基)-2H-1,2,4-3-氨基-1,2,4-三氮唑；5-(4-甲氧苯基)-1H-1,2,4-3-氨基-1,2,4-三氮唑
• 英文名称: 3-(4-methoxyphenyl)-1H-1,2,4-triazol-5-amine
• 英文别名: 5-(4-methoxyphenyl)-1H-1,2,4-triazol-3-amine
• CAS: 54464-14-1
• 化学式: C₉H₁₀N₄O
• mdl: MFCD00815477
• 分子量: 190.205
• InChiKey: BKEAHUXWMIWWCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  76.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-(4-Methoxyphenyl)-4h-1,2,4-triazol-3-amine
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-(4-Methoxyphenyl)-4h-1,2,4-triazol-3-amine
CAS number: 54464-14-1

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H10N4O
Molecular weight: 190.2

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(4-甲氧基苯基)-4H-1,2,4-三唑-3-胺 在 boron trifluoride methanol complex 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 93.0h， 生成 7-chloro-6-(2-chloroethyl)-2-(4-methoxyphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  心血管药物的研究。6.与杂环系统融合的1,2,4-三唑并[1,5-a]嘧啶的合成及其冠状血管舒张和降压活性。

  摘要：

  描述了与吡咯，噻吩，吡喃，吡啶和哒嗪融合的1,2,4-三唑并[1,5-a]嘧啶的合成及其冠状血管舒张和降压活性。在这些化合物中，8-叔丁基-7,8-二氢-5-甲基-6H-吡咯并[3,2-e] [1,2,4]三唑并[1,5-a]嘧啶（23）为被发现是最有前途的潜在心血管疾病药物，已被证明比特拉迪尔[7-二乙基氨基）-5-甲基-1,2,4-三唑并[1,5-a]嘧啶具有更强的冠脉扩张活性，降压活性与硫酸胍乙当量相当。

  DOI：

  10.1021/jm00182a021
• 作为产物：
  描述：

  N-(4-methoxybenzamido)-guanidine 在 sodium hydroxide 作用下， 反应 36.0h， 以69%的产率得到5-(4-甲氧基苯基)-4H-1,2,4-三唑-3-胺
  参考文献：
  名称：

  高效微管蛋白聚合抑制剂的发现：新型 2,7-二芳基-[1,2,4] 三唑并 [1,5-a] 嘧啶的设计、合成和构效关系

  摘要：

  通过去除我们之前报道的化合物3 中的5-甲基和 6-乙酰基，我们设计了一系列新型 2,7-二芳基-[1,2,4] 三唑并 [1,5- a ] 嘧啶衍生物作为潜在的微管蛋白聚合抑制剂。其中，化合物5e对 HeLa 细胞显示出低纳摩尔的抗增殖功效，比铅类似物3高 166 倍。有趣的是，与 HEK-293（正常人胚胎肾细胞）相比，5e在抑制癌细胞方面表现出显着的选择性。此外，5e通过改变 p-cdc2 和细胞周期蛋白 B1 的表达水平，剂量依赖性地将 HeLa 阻滞在 G2/M 期，并通过调节裂解的 PARP 的表达导致 HeLa 细胞凋亡。进一步的证据表明，5e有效地抑制了微管蛋白聚合，并且比阳性对照 CA-4 强 3 倍。此外，分子对接分析表明，5e与秋水仙碱结合位点中的 CA-4 重叠良好。这些研究表明，2,7-二芳基-[1,2,4]三唑并[1,5- a ]嘧啶骨架可用作开发新型微管蛋白聚合抑制剂作为潜在抗癌剂的主要单元。

  DOI：

  10.1016/j.ejmech.2021.113449

文献信息

• Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors
  作者：Simon Platte、Marvin Korff、Lukas Imberg、Ilker Balicioglu、Catharina Erbacher、Jonas M. Will、Constantin G. Daniliuc、Uwe Karst、Dmitrii V. Kalinin

  DOI：10.1002/cmdc.202100431

  日期：2021.12.14

  approach toward N-acylated aminotriazoles is reported, enabling the compounds’ screening against FXIIa and thrombin. This approach afforded low-nanomolar FXIIa and thrombin inhibitors with no off-targeting of the other tested serine proteases. Selected compounds were shown to be covalent inhibitors of FXIIa and demonstrated anticoagulant properties in vitro, influencing the intrinsic blood coagulation

  抗凝剂进展：报道了一种 N-酰化氨基三唑的微量平行合成方法，使该化合物能够针对 FXIIa 和凝血酶进行筛选。这种方法提供了低纳摩尔浓度的 FXIIa 和凝血酶抑制剂，且其他测试的丝氨酸蛋白酶没有脱靶。选定的化合物被证明是 FXIIa 的共价抑制剂，并在体外表现出抗凝血特性，影响内在的凝血途径。
• [EN] AMINOTRIAZOLE IMMUNOMODULATORS FOR TREATING AUTOIMMUNE DISEASES<br/>[FR] IMMUNOMODULATEURS D'AMINOTRIAZOLE POUR TRAITER DES MALADIES AUTO-IMMUNES
  申请人：UNIV ROCKEFELLER

  公开号：WO2017123518A1

  公开（公告）日：2017-07-20

  1-Acyl-3-(heteroaryl)-1H-1,2,4-triazol-5-amines of formula (I) are disclosed. These compounds inhibit Coagulation Factor XIIa in the presence of thrombin and other coagulation factors. They are useful to treat autoimmune diseases.

  1-酰基-3-(杂芳基)-1H-1,2,4-三唑-5-胺的公式(I)化合物被公开。这些化合物在存在凝血酶和其他凝血因子时抑制凝血因子XIIa。它们可用于治疗自身免疫疾病。
• A Novel Iron-catalyzed One-pot Synthesis of 3-Amino-1,2,4-triazoles
  作者：Taoufik Rohand、Victor N. Mkpenie、Mohammadine El Haddad、István E. Markó

  DOI：10.1002/jhet.3450

  日期：2019.2

  A novel one‐pot synthesis of 3‐amino‐1,2,4‐triazole developed via iron (III) catalyzed route is reported. The new method is more efficient, simple, and convenient and presents a concise new strategy for the synthesis of 3‐amino‐1,2,4‐triazole derivatives. The iron (III) complex intermediate assisted in the intramolecular bond cyclization owing to its Lewis acidity or oxidizing properties. A series

  据报道，通过铁（III）催化途径开发的一种新型一锅法合成3-氨基1,2,4-三唑。该新方法更加高效，简单和方便，为合成3‐氨基1,2,4‐三唑衍生物提出了一种简洁的新策略。铁（III）配合物中间体由于其路易斯酸度或氧化特性而有助于分子内键的环化。还研究了一系列在对位和/或邻位带有取代的给电子和吸电子基团的芳族腈。取代基的位置影响最终化合物的收率，对位取代的底物收率相对较高。
• Discovery of 7-alkyloxy- [1,2,4] triazolo[1,5-a] pyrimidine derivatives as selective positive modulators of GABAA1 and GABAA4 receptors with potent antiepileptic activity
  作者：Jun Wu、Zhipeng Hou、Yan Wang、Liping Chen、Chengxi Lian、Qingfei Meng、Chaoying Zhang、Xiufen Li、Longjiang Huang、Haibo Yu

  DOI：10.1016/j.bioorg.2021.105565

  日期：2022.2

  Further studies demonstrated that the anticonvulsant activity of these compounds mainly depended on their allosteric potentiation of GABAA receptors. Among them, compound 10c was picked for the mechanism study due to its potent activity. The compound is more sensitive to subunit configurations of synaptic α1β2γ2 and extrasynaptic α4β3δ GABAA receptors, but there were no effects on NMDA receptors and Nav1

  设计合成了一系列7-烷氧基-[1,2,4]三唑并[1,5-a]嘧啶衍生物。最大电击 (MES) 和戊四唑 (PTZ) 测试用于评估其抗惊厥活性。该系列化合物中的大多数都表现出显着的抗癫痫作用。进一步的研究表明，这些化合物的抗惊厥活性主要取决于它们对 GABA A受体的变构增强作用。其中，化合物10c因其强大的活性而被选中进行机理研究。该化合物对突触 α1β2γ2 和突触外 α4β3δ GABA A受体的亚基构型更敏感，但对 NMDA 受体和 Nav1.2 钠通道没有影响。同时，10c作用于不同于常用抗惊厥药苯二氮卓类和巴比妥类药物的 GABA A受体位点。此外，对天然神经元的研究表明，化合物10c还增强了天然 GABA A受体的活性，并降低了培养的皮层神经元的动作电位放电。这种结构化合物可能为进一步设计新型抗癫痫分子奠定基础。
• 3-Aryl/Heteroaryl-5-amino-1-(3′,4′,5′-trimethoxybenzoyl)-1,2,4-triazoles as antimicrotubule agents. Design, synthesis, antiproliferative activity and inhibition of tubulin polymerization
  作者：Romeo Romagnoli、Filippo Prencipe、Paola Oliva、Stefania Baraldi、Pier Giovanni Baraldi、Andrea Brancale、Salvatore Ferla、Ernest Hamel、Roberta Bortolozzi、Giampietro Viola

  DOI：10.1016/j.bioorg.2018.06.037

  日期：2018.10

  at the 3-position of the 5-amino-1,2,4-triazole system. Most of the twenty-two tested compounds showed moderate to potent antiproliferative activities against a panel of solid tumor and leukemic cell lines, with four (5j, 5k, 5o and 5p) showing strong antiproliferative activity (IC50 < 1 μM) against selected cancer cells. Among them, several molecules preferentially inhibited the proliferation of leukemic

  已知许多天然和合成物质会干扰微管蛋白的动态组装，从而阻止微管的形成。在我们寻找有效的和选择性的抗肿瘤剂中，合成了一系列新的1-（3'，4'，5'-三甲氧基苯甲酰基）-5-氨基-1,2,4-三唑。这些化合物具有不同的杂环，包括噻吩，呋喃或三个同分异构的吡啶，并且它们在5-氨基-1,2,4-三唑体系的3位上具有带电子释放或吸电子取代基的苯环。 。测试的22种化合物中的大多数对一组实体瘤和白血病细胞系均显示出中度至强效的抗增殖活性，其中4种（5j，5k，5o和5p） 对选定的癌细胞显示出强大的抗增殖活性（IC 50 <1μM）。其中，有几种分子优先抑制白血病细胞系的增殖，显示Jurkat和RS4; 11细胞的IC 50值比源自实体瘤的三系（HeLa，HT-29和MCF- 7个单元格）。化合物5k强烈抑制微管蛋白组装，IC 50值为0.66μM，是在CA-4的同时实验中获得的一半（IC 50  =