4-甲酰基-N,N-二甲基-1H-咪唑-1-磺酰胺 | 140174-48-7

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-甲酰基-N,N-二甲基-1H-咪唑-1-磺酰胺
• 英文名称: 4-formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide
• 英文别名: 1-(dimethylsulfamoyl)-4-imidazolecarboxaldehyde；4-formylimidazole-1-sulfonic acid dimethylamide；1-dimethylsulfamoylimidazol-4-carbaldehyde；1-N,N-dimethylaminosulfonyl-4-formyl-1H-imidazole；4-formyl-imidazole-1-sulfonic acid dimethylamide；1-(dimethylsulphamoyl)-4-formylimidazole；4-formyl-N,N-dimethylimidazole-1-sulfonamide
• CAS: 140174-48-7
• 化学式: C₆H₉N₃O₃S
• mdl: MFCD09800947
• 分子量: 203.222
• InChiKey: BBTZETLXNQDZKF-UHFFFAOYSA-N

物化性质

• 沸点：
  383.7±34.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide
Synonyms: N,N-Dimethyl 4-formyl-1H-imidazole-1-sulfonamide

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
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: 4-Formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide
CAS number: 140174-48-7

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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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H9N3O3S
Molecular weight: 203.2

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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：

  4-甲酰基-N,N-二甲基-1H-咪唑-1-磺酰胺 在 3-苄基羟乙基甲基噻唑氯化锂 、 三乙胺 作用下， 以 甲醇 为溶剂， 以96%的产率得到
  参考文献：
  名称：

  TIMPZ：金属/氢配位聚合物的精致构建基块

  摘要：

  描述了新型的多硝化配体四[4（5）-咪唑基]吡嗪（TIMPZ，1）及其Fe II的络合物。这种配体具有出色的通过氢键或金属螯合在1D超结构中聚集的能力。TIMPZ显示了对超分子组装的前所未有的构象控制。金属或氢配位切换了驱动装配偏好的外围环的构型。对于[Fe n（TIMPZ）n +1 ] 2n +配合物，UV / Vis光谱显示出主可见吸收带的红移，其中“ n”值。TIMPZ还具有氢键触发的激发态分子内质子转移（ESIPT）荧光，与过渡金属螯合可完全抑制这种荧光。

  DOI：

  10.1002/ejic.201900229
• 作为产物：
  描述：

  1-dimethylsulfamoyl-5-imidazolecarboxaldehyde 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以32 mg的产率得到4-甲酰基-N,N-二甲基-1H-咪唑-1-磺酰胺
  参考文献：
  名称：

  Kim, Jang-Woo; Abdelaal, Salma M.; Bauer, Ludwig, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 2, p. 611 - 620

  摘要：

  DOI：

文献信息

• Design of Coordination Interaction of Zn(II) Complex with Oligo-Aspartate Peptide to Afford a High-Affinity Tag–Probe Pair
  作者：Hirokazu Fuchida、Shigekazu Tabata、Naoya Shindo、Ippei Takashima、Qiao Leng、Yuji Hatsuyama、Itaru Hamachi、Akio Ojida

  DOI：10.1246/bcsj.20150037

  日期：2015.6.15

  A complementary recognition pair consisting of a genetically encodable peptide tag and a small molecular probe is a powerful tool to specifically label and manipulate a protein of interest under biological conditions. In this study, we report the redesign of a tag–probe pair comprising an oligo-aspartate peptide tag (such as DDDD) and a binuclear zinc complex. Isothermal-titration calorimetry screening of binding between the series of peptides and zinc complexes revealed that the binding affinity was largely influenced by subtle changes of the ligand structure of the probe. However, the binding was tolerant to differences of the tag peptide sequence. Of those tested, a pair containing a peptide tag (DDAADD) and a binuclear zinc complex possessing 4-chloropyridines (3-2Zn(II)) showed the strongest binding affinity (Ka = 3.88 × 105 M−1), which was about 10-fold larger than the conventional pair of D4-peptide tag (DDDD) and 1-2Zn(II) containing nonsubstituted pyridines (Ka = 3.73 × 104 M−1). The strong binding of this new complementary recognition pair enabled the rapid covalent labeling of a tag-fused maltose binding protein with a fluorescent zinc complex, demonstrating its potential utility in protein analysis.

  一种由遗传编码可表达的多肽标签和小分子探针组成的互补识别对，是在生物条件下特异性地标记和操控感兴趣蛋白的有力工具。本研究中，我们报道了一种标签-探针对的设计重构，该对由寡天冬氨酸多肽标签（如DDDD）和双核锌复合物组成。等温滴定量热法筛选一系列多肽与锌复合物之间的结合发现，结合亲和力主要受探针配体结构的细微变化影响。然而，结合对标签多肽序列的差异具有容忍性。在测试的组合中，包含多肽标签（DDAADD）和含4-氯吡啶的双核锌复合物（3-2Zn(II)）的组合显示出最强的结合亲和力（Ka = 3.88 × 105 M−1），比传统的D4多肽标签（DDDD）与不含取代吡啶的1-2Zn(II)组合的亲和力大约强10倍（Ka = 3.73 × 104 M−1）。这种新的互补识别对强大的结合力使得能够快速共价标记融合了标签的麦芽糖结合蛋白与荧光锌复合物，展示了其在蛋白质分析中的潜在应用价值。
• A Photoswitchable Agonist for the Histamine H ₃ Receptor, a Prototypic Family A G‐Protein‐Coupled Receptor
  作者：Niels J. Hauwert、Tamara A. M. Mocking、Daniel Da Costa Pereira、Ken Lion、Yara Huppelschoten、Henry F. Vischer、Iwan J. P. De Esch、Maikel Wijtmans、Rob Leurs

  DOI：10.1002/anie.201813110

  日期：2019.3.26

  Spatiotemporal control over biochemical signaling processes involving G protein‐coupled receptors (GPCRs) is highly desired for dissecting their complex intracellular signaling. We developed sixteen photoswitchable ligands for the human histamine H3 receptor (hH3R). Upon illumination, key compound 65 decreases its affinity for the hH3R by 8.5‐fold and its potency in hH3R‐mediated Gi protein activation by

  解剖G蛋白偶联受体（GPCR）的生化信号转导过程时空控制是非常需要的。我们为人类组胺H 3受体（hH 3 R）开发了16种光开关配体。照射时，键化合物65降低了其为HH的亲和力3由R 8.5倍及在HH效力3 R-介导ģ我通过在蛋白活化20倍，与反式和顺式异构体都用作完全激动剂。在非洲爪蟾卵母细胞中进行实时两电极电压钳实验，65显示了光诱导的hH 3 R活性的快速调节。配体65在组胺受体亚家族之间显示出良好的结合选择性，并且具有良好的光解稳定性。总而言之，65（VUF15000）是第一个被证实在光切换时通过其亲和力和效力而被调节且同时保持其固有活性的光可切换GPCR激动剂，从而使其成为一种用于时空控制GPCR活化的新化学生物学工具。
• Synthesis and Evaluation of Imidazolylmethylenetetrahydronaphthalenes and Imidazolylmethyleneindanes:  Potent Inhibitors of Aldosterone Synthase
  作者：Sarah Ulmschneider、Ursula Müller-Vieira、Markus Mitrenga、Rolf W. Hartmann、Sandrine Oberwinkler-Marchais、Christian D. Klein、Matthias Bureik、Rita Bernhardt、Iris Antes、Thomas Lengauer

  DOI：10.1021/jm049600p

  日期：2005.3.1

  Elevated plasma aldosterone levels play a detrimental role in certain forms of congestive heart failure and myocardial fibrosis. We proposed aldosterone synthase (CYP11B2) as a novel target for the treatment of these diseases. In this study, the synthesis and biological evaluation of substituted E- and Z-imidazolylmethylenetetrahydronaphthalenes and E- and Z-imidazolylmethyleneindanes (compounds 1a

  血浆醛固酮水平升高在某些形式的充血性心力衰竭和心肌纤维化中起有害作用。我们提出了醛固酮合酶（CYP11B2）作为治疗这些疾病的新目标。在这项研究中，描述了取代的E-和Z-咪唑基亚甲基四氢萘以及E-和Z-咪唑基亚甲基茚满（化合物1a，b-9a，b）的合成和生物学评估。该化合物通过类似Wittig的反应制备。使用裂变酵母和V79 MZh细胞中表达的牛CYP11B和人CYP11B2对其活性进行了测试。确定了对人CYP11B1，CYP19和CYP17的选择性。尤其是在CYP11B1（类固醇11β-羟化酶）的情况下，选择性是一个关键问题，因为该酶与目标酶之间的序列同源性非常高（93％）。基于人CYP2C9的X射线结构，建立了CYP11B2的蛋白质模型，并与标题化合物进行了对接实验。生物学结果显示CYP11B2的高效抑制剂（IC（50）= 4-93 nM）。Z-异构体通常比相应的E-异构体更具活性。可
• [EN] NEW COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2013061077A1

  公开（公告）日：2013-05-02

  The invention relates to new naphthyridine derivative compounds, to pharmaceutical compositions comprising said compounds, to processes for the preparation of said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

  这项发明涉及新的萘啉衍生物化合物，包括所述化合物的药物组合物，制备所述化合物的方法以及利用所述化合物治疗疾病，例如癌症。
• Functionalization of the Imidazole Backbone by Means of a Tailored and Optimized Oxidative Heck Cross‐Coupling
  作者：Davide Cirillo、Francesco Angelucci、Hans‐René Bjørsvik

  DOI：10.1002/adsc.202000909

  日期：2020.11.18

  and selective Pd‐catalyzed cross‐coupling of aromatic boronic acids with vinyl‐imidazoles is disclosed. Unlike most cross‐coupling reactions, this method operates well in absence of bases avoiding the formation of by‐products. The reactivity is highly enhanced by the presence of nitrogen‐based ligands, in particular bathocuproine. The method involves MnO2 as oxidant for the oxidation Pd (0)→Pd (II), a

  公开了芳族硼酸与乙烯基咪唑的一般和选择性Pd催化交叉偶联。与大多数交叉偶联反应不同，该方法在没有碱的情况下运行良好，避免了副产物的形成。氮基配体（特别是红霉素）的存在可大大提高反应性。该方法涉及MnO 2作为氧化Pd（0）→Pd（II）的氧化剂，它比以前文献中报道的要弱得多。这允许使用具有多个官能团的反应物。范围和限度研究涉及一系列24种硼酸，其中18种提供的TM产率在41–95％范围内。所公开的方法构成了在咪唑支架上进行氧化性Heck交叉偶联的第一种通用方法，该方法还可以与其他杂环一起选择。