噻吩-3-甲胺肟 | 58905-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 噻吩-3-甲胺肟
• 中文别名: 噻吩-3-甲胺肟,97；噻吩-3-甲脒
• 英文名称: N'-hydroxythiophene-3-carboximidamide
• CAS: 58905-71-8
• 化学式: C₅H₆N₂OS
• mdl: MFCD01313358
• 分子量: 142.181
• InChiKey: KLQUDAATMCQZEF-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C(Solv: benzene (71-43-2))
• 沸点：
  258.7±32.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
N’-Hydroxythiophene-3-carboximidamide
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
N’-Hydroxythiophene-3-carboximidamide
Ingredient name:
CAS number: 58905-71-8

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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: C5H6N2OS
Molecular weight: 142.2

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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, 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：

  噻吩-3-甲胺肟 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 methyl N-[3-(3-thiophen-3-yl-1,2,4-oxadiazol-5-yl)propyl]carbamate
  参考文献：
  名称：

  扩大了二取代的1,2,4-恶二唑的可合成空间

  摘要：

  优化了从羧酸和腈的一锅法合成3,5-二取代的1,2,4-恶二唑的平行化学反应。该方法已在141个成员库中得到验证；以高成功率和中等收率回收了所需的产品。该方法在生物活性化合物吡非索和游离脂肪酸受体1激动剂的合成中得到了实际应用。在此基础上，列举了4 948 100种可合成的药物样3,5-二取代1,2,4-恶二唑类化合物。方法和可用的经过验证的试剂。

  DOI：

  10.1021/acscombsci.6b00103
• 作为产物：
  描述：

  3-噻吩甲醛 在 ammonium hydroxide 、 盐酸羟胺 、 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 噻吩-3-甲胺肟
  参考文献：
  名称：

  新型 1,2,4-恶二唑/吡咯烷杂化物作为拓扑异构酶 IV 和 DNA 促旋酶抑制剂，具有良好的抗菌活性

  摘要：

  合成了一系列具有 1,2,4-恶二唑部分的杂化吡咯烷化合物，以开发针对 DNA 促旋酶和拓扑异构酶 IV (Topo IV) 的有效分子。化合物8-20是基于我们实验室先前公开的一系列化合物开发的，但为了提高化合物的生物活性而进行了小的结构修改。与新生霉素相比，IC 50  = 170 nM，DNA 促旋酶抑制试验的结果显示化合物16和17是所有合成衍生物中最有效的，IC 50值分别为 180 和 210 nM。化合物17对所有合成化合物的大肠杆菌Topo IV，IC 50值为13 µM，与新生霉素相当（IC 50  = 11 µM）。因此，杂种16和17似乎是潜在的双靶点抑制剂。在最小抑制浓度 (MIC) 测定中，化合物17对大肠杆菌的表现优于环丙沙星，MIC 为 55 ng/ml，而环丙沙星为 60 ng/ml。最后，对接研究以及体外实验支持了我们有希望的方法来有效开发有效的先导物，以进一步优化作为双

  DOI：

  10.1002/ardp.202100516

文献信息

• Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety
  作者：Marina Tarasenko、Nikolay Duderin、Tatyana Sharonova、Sergey Baykov、Anton Shetnev、Alexey V. Smirnov

  DOI：10.1016/j.tetlet.2017.08.020

  日期：2017.9

  An efficient and mild one-pot protocol has been developed for the synthesis of 1,2,4-oxadiazoles via the reaction of amidoximes with dicarboxylic acid anhydrides in a NaOH/DMSO medium. The method allows the synthesis of diversely substituted carboxylic acids bearing the 1,2,4-oxadiazole motif, – a popular building block for pharmaceutical research, in moderate to excellent yields. The reaction scope

  已经开发了一种有效且温和的一锅操作规程，用于通过a胺肟与二羧酸酐在NaOH / DMSO介质中的反应来合成1,2,4-恶二唑。该方法可以合成具有1,2,4-恶二唑基序的不同取代的羧酸，该基团是药物研究的常用组成部分，产率中等至优异。反应范围包括芳族和杂芳族酰胺肟以及五元，六元和七元酸酐。该方法的优点是证明了克级可缩放性和使用廉价的起始原料，从工艺化学的角度来看，这对于将来的工业应用至关重要。
• Whole cell screen based identification of spiropiperidines with potent antitubercular properties
  作者：Subramanyam J. Tantry、Giulia Degiacomi、Sreevalli Sharma、Lalit kumar Jena、Ashwini Narayan、Supreeth Guptha、Gajanan Shanbhag、Sreenivasaiah Menasinakai、Meenakshi Mallya、Disha Awasthy、Gayathri Balakrishnan、Parvinder Kaur、Deepa Bhattacharjee、Chandan Narayan、Jitendar Reddy、C.N. Naveen Kumar、Radha Shandil、Francesca Boldrin、Marcello Ventura、Riccardo Manganelli、Ruben C. Hartkoorn、Stewart T. Cole、Manoranjan Panda、Shankar D. Markad、Vasanthi Ramachandran、Sandeep R. Ghorpade、Neela Dinesh

  DOI：10.1016/j.bmcl.2015.05.087

  日期：2015.8

  non-replicating (NRP) conditions, resulted in the identification of multiple, novel but structurally related spiropiperidines with potent antitubercular properties. These compounds could be further classified into three classes namely 3-(3-aryl-1,2,4-oxadiazol-5-yl)-1′-alkylspiro[indene-1,4′-piperidine] (abbr. spiroindenes), 4-(3-aryl-1,2,4-oxadiazol-5-yl)-1′-alkylspiro[chromene-2,4′-piperidine] (abbr. spirochromenes)

  在复制和非复制（NRP）条件下进行的基于全细胞的筛选，以鉴定抗结核分枝杆菌（Mtb）的命中物，从而鉴定出具有有效抗结核特性的多种新颖但与结构相关的螺哌啶。这些化合物可进一步分为三类，即3-（3-芳基-1,2,4-恶二唑-5-基）-1'-烷基螺[茚-1,4'-哌啶]（螺环茚）， 4-（3-芳基-1,2,4-恶二唑-5-基）-1'-烷基螺[色烯-2,4'-哌啶]（螺螺铬烯）和1'-苄基螺[吲哚-1,4 ′-哌啶] -2（1 H）-1 （螺旋螺吲哚）。螺茚显示⩾4log 10在复制的Mtb上杀死（2–12μM），但在非复制条件下具有中等活性。螺环茚抗性突变体的全基因组测序工作导致鉴定了MmpL3（大分枝杆菌膜蛋白）中的I292L突变，这是将霉菌酸组装到Mtb的细胞壁核心中所必需的。MIC调制研究表明，该突变体对螺环色酮具有交叉抗性，但对螺线吲哚酮不具有交叉抗性。该信函描述了铅鉴定工作，旨在提高效
• Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence
  作者：Sofia Presnukhina、Marina Tarasenko、Sergey Baykov、Sergey N. Smirnov、Vadim P. Boyarskiy、Anton Shetnev、Mikhail K. Korsakov

  DOI：10.1016/j.tetlet.2019.151543

  日期：2020.2

  and convenient one-pot method is reported for the synthesis of (E)-3-(3-aryl(heteroaryl, alkyl)-1,2,4-oxadiazole-5-yl)acrylic acids utilizing readily accessible or commercially available substituted benzamidoximes and inexpensive exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. The method is based on the reaction of amidoximes with the anhydride in a basic medium at RT followed by an acid-catalyzed

  据报道一种简单方便的一锅法，利用易于获得或可商购的方法合成（E）-3-（3-芳基（杂芳基，烷基）-1，2，4-恶二唑-5-基）丙烯酸。取代的苯甲酰胺肟和廉价的exo -3,6-环氧-1,2,3,6-四氢邻苯二甲酸酐。该方法基于在室温下碱性介质中in胺肟与酸酐的反应，然后进行酸催化的逆-Diels-Alder反应。观察到的立体选择性杂环化/逆-Diels-Alder级联过程适用于合成各种取代的（E）-1,2,4-恶二唑-5-基丙烯酸，其芳基部分具有供电子基团和吸电子基团，并且在1,2,4-恶二唑环的3位具有杂芳基或烷基取代基（42-79 ％； 15个示例）。
• Discovery of highly potent triazoleantifungal agents with piperidine-oxadiazole side chains
  作者：Xiaomeng He、Yan Jiang、Yongqiang Zhang、Shanchao Wu、Guoqiang Dong、Na Liu、Yang Liu、Jianzhong Yao、Zhenyuan Miao、Yan Wang、Wannian Zhang、Chunquan Sheng

  DOI：10.1039/c4md00505h

  日期：——

  A series of novel triazole antifungal agents containing piperidine-oxadiazole side chains were designed and synthesized. Compound11bwas highly active againstCandida albicanswith a MIC value of 0.016 μg mL⁻¹.

  一系列含有哌啶-噁二唑侧链的新型三唑类抗真菌药物被设计并合成。化合物11b 对白念珠菌表现出高活性，最小抑菌浓度（MIC）值为0.016 μg/mL。
• [EN] COMPOUNDS FOR MODULATING S1P1 ACTIVITY AND METHODS OF USING THE SAME<br/>[FR] COMPOSÉS POUR MODULER L'ACTIVITÉ DE S1P1 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：TREVENA INC

  公开号：WO2018231745A1

  公开（公告）日：2018-12-20

  The present embodiments are directed, in part, to compounds, or pharmaceutically acceptable salts thereof, or pharmaceutical compositions thereof for modulating the activity of S1P1 receptor and methods of using the same.

  目前的实施例部分涉及化合物，或其药学上可接受的盐，或用于调节S1P1受体活性的药物组合物，以及使用它们的方法。