1-甲基-2-氧代-5-吲哚啉磺酰氯 | 166883-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-甲基-2-氧代-5-吲哚啉磺酰氯
• 中文别名: 1-甲基-2-氧代-5-吲哚林磺酰氯
• 英文名称: 1-methyl-2-oxoindoline-5-sulfonyl chloride
• 英文别名: 1-methyl-2-oxo-3H-indole-5-sulfonyl chloride
• CAS: 166883-20-1
• 化学式: C₉H₈ClNO₃S
• mdl: MFCD08691362
• 分子量: 245.686
• InChiKey: YFRKJJDSYAKRAU-UHFFFAOYSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  496.0±45.0 °C(Predicted)
• 密度：
  1.509±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  C
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P260,P264,P270,P280,P301+P312,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P321,P330,P363,P405,P501
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H314
• 储存条件：
  温度：2-8℃，惰性气氛环境下

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Methyl-2-oxo-5-indolinesulfonyl chloride
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: 1-Methyl-2-oxo-5-indolinesulfonyl chloride
CAS number: 166883-20-1

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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.
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: C9H8ClNO3S
Molecular weight: 245.7

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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, hydrogen chloride, 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：

  1-甲基-2-氧代-5-吲哚啉磺酰氯 在 potassium cyanide 、 硫酸 、 碘 、 sodium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 69.75h， 生成 5-[[4-[(2S,4R)-4-hydroxy-2-methyl-tetrahydropyran-4-yl]-2-thienyl]sulfanyl]-1-methyl-indolin-2-one
  参考文献：
  名称：

  Efficient Syntheses of AZD4407 via Thioether Formation by Nucleophilic Attack of Organometallic Species on Sulphur

  摘要：

  The development of two efficient strategies for the synthesis of AZD4407 is reported, both of which are considered suitable for large-scale manufacture. In the first approach, 3-bromothiophene is coupled with (2S)-2-methyltetrahydropyran-4one using Grignard chemistry. Following hydroxyl protection and lithiation at thiophene C-2, reaction with a protected 5-mercapto-1-methyl-1,3-dihydro-indol-2-one derivative bearing a leaving group on sulphur provides AZD4407 after acid-catalysed deprotection and epimerisation. The second approach starts from 2,4-dibromothiophene, which undergoes a selective Grignard exchange reaction at C-2 followed by reaction with similar protected mercapto-oxindole derivatives. Reprotection of the oxindole ring, followed by a second Grignard exchange, and reaction with (2S)-2-methyltetrahydropyran-4-one provides AZD4407 after acid-catalysed deprotection and epimerisation.

  DOI：

  10.1021/op0500483
• 作为产物：
  描述：

  N-甲基吲哚酮 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 1-甲基-2-氧代-5-吲哚啉磺酰氯
  参考文献：
  名称：

  Efficient Syntheses of AZD4407 via Thioether Formation by Nucleophilic Attack of Organometallic Species on Sulphur

  摘要：

  The development of two efficient strategies for the synthesis of AZD4407 is reported, both of which are considered suitable for large-scale manufacture. In the first approach, 3-bromothiophene is coupled with (2S)-2-methyltetrahydropyran-4one using Grignard chemistry. Following hydroxyl protection and lithiation at thiophene C-2, reaction with a protected 5-mercapto-1-methyl-1,3-dihydro-indol-2-one derivative bearing a leaving group on sulphur provides AZD4407 after acid-catalysed deprotection and epimerisation. The second approach starts from 2,4-dibromothiophene, which undergoes a selective Grignard exchange reaction at C-2 followed by reaction with similar protected mercapto-oxindole derivatives. Reprotection of the oxindole ring, followed by a second Grignard exchange, and reaction with (2S)-2-methyltetrahydropyran-4-one provides AZD4407 after acid-catalysed deprotection and epimerisation.

  DOI：

  10.1021/op0500483

文献信息

• Targeting quinolone- and aminocoumarin-resistant bacteria with new gyramide analogs that inhibit DNA gyrase
  作者：Katherine A. Hurley、Thiago M. A. Santos、Molly R. Fensterwald、Madhusudan Rajendran、Jared T. Moore、Edward I. Balmond、Brice J. Blahnik、Katherine C. Faulkner、Marie H. Foss、Victoria A. Heinrich、Matthew G. Lammers、Lucas C. Moore、Gregory D. Reynolds、Galen P. Shearn-Nance、Brian A. Stearns、Zi W. Yao、Jared T. Shaw、Douglas B. Weibel

  DOI：10.1039/c7md00012j

  日期：——

  potent inhibitors of DNA gyrase and are active against clinical strains of Gram-negative bacteria (Escherichia coli, Shigella flexneri, and Salmonella enterica; 3 of 10 wild-type strains tested) and Gram-positive bacteria (Bacillus spp., Enterococcus spp., Staphylococcus spp., and Streptococcus spp.; all 9 of the wild-type strains tested). E. coli strains resistant to the DNA gyrase inhibitors ciprofloxacin

  细菌DNA促旋酶是一种必不可少的II型拓扑异构酶，可使细胞克服复制，转录，重组和修复过程中遇到的拓扑障碍。该酶在细菌中无处不在，代表了抗菌治疗的重要临床目标。在本文中，我们从183个衍生物库中报告了三种激动人心的新型回旋酰胺类似物的表征，它们是DNA回旋酶的有效抑制剂，对革兰氏阴性菌（大肠杆菌，志贺氏志贺氏菌和肠炎沙门氏菌；测试的10种野生型菌株中有3种）和革兰氏阳性菌（芽孢杆菌，肠球菌，葡萄球菌spp。，and Streptococcus spp .; 所有9种野生型菌株都进行了测试）。对DNA促旋酶抑制剂环丙沙星和新霉素具有抗性的大肠杆菌菌株对这些新的乙二酰胺具有极小的交叉抗性。体外研究表明，新的类似物可有效抑制DNA促旋酶的DNA超螺旋活性（IC 50值为47–170 nM），但不会改变酶的ATPase活性。尽管赋予细菌细胞对这些新的回旋酰胺抗性的突变会映射到编码DNA回旋酶亚基的基
• Discovery of 3-(4-(2-((1<i>H</i>-Indol-5-yl)amino)-5-fluoropyrimidin-4-yl)-1<i>H</i>-pyrazol-1-yl)propanenitrile Derivatives as Selective TYK2 Inhibitors for the Treatment of Inflammatory Bowel Disease
  作者：Chufeng Zhang、Wenyan Qi、Yong Li、Minghai Tang、Tao Yang、Kongjun Liu、Yong Chen、Dexin Deng、Mingli Xiang、Lijuan Chen

  DOI：10.1021/acs.jmedchem.0c01468

  日期：2021.2.25

  IFN-driven responses that are critical in immune-mediated diseases. Herein, we report the design, synthesis, and structure–activity relationships (SARs) of 3-(4-(2-((1H-indol-5-yl)amino)-5-fluoropyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile derivatives as selective TYK2 inhibitors. Among them, compound 14l exhibited acceptable TYK2 inhibition with an IC50 value of 9 nM, showed satisfactory selectivity

  TYK2 介导 IL-23、IL-12 和 I 型 IFN 驱动反应的信号传导，这些反应对于免疫介导的疾病至关重要。在此，我们报告了 3-(4-(2-((1 H -indol-5-yl)amino)-5-氟嘧啶-4-yl)-1 的设计、合成和构效关系 (SAR) H-吡唑-1-基)丙腈衍生物作为选择性 TYK2 抑制剂。其中，化合物14l表现出可接受的TYK2抑制作用，IC 50值为9 nM，与其他三种同源JAK激酶相比表现出令人满意的选择性特性，并且在淋巴细胞系和人全血的JAK/STAT信号通路中表现出良好的功能效力。在肝微粒体测定研究中， 14l的清除率和半衰期分别为11.4 mL/min/g和121.6 min。此外，在葡聚糖硫酸钠结肠炎模型中， 14l减少了促炎细胞因子IL-6和TNF-α的产生，改善了粘膜浸润、增厚和水肿的炎症症状。综上所述， 14l是一种选择性TYK2抑制剂，可用于治疗免疫性疾病，值得进一步研究。
• [EN] SUBSTITUTED OCTAHYDROPYRROLO[1,2-A]PYRAZINE SULFONAMIDES AS CALCIUM CHANNEL BLOCKERS<br/>[FR] OCTAHYDROPYRROLO[1,2-A]PYRAZINE SULFONAMIDES SUBSTITUÉS À TITRE D'INHIBITEURS DES CANAUX CALCIQUES
  申请人：ABBVIE INC

  公开号：WO2013049174A1

  公开（公告）日：2013-04-04

  The present application relates to: (a) compounds of Formula (I): (I), and salts thereof, wherein Z', Z", L2, G2, R1, and R2 are as defined in the specification; (b) compositions comprising such compounds and salts; and (c) methods of use of such compounds, salts, and compositions, particularly use as calcium channel blockers.

  本申请涉及：(a) 公式(I)的化合物及其盐，其中Z'、Z"、L2、G2、R1和R2如规范中所定义；(b) 包含这些化合物和盐的组合物；以及(c) 使用这些化合物、盐和组合物的方法，特别是用作钙通道阻滞剂。
• DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS
  申请人：Armani Elisabetta

  公开号：US20130005716A1

  公开（公告）日：2013-01-03

  Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols are useful as inhibitors of the phosphodiesterase 4 (PDE4) enzyme and the treatment of certain conditions such as COPD.

  1-苯基-2-吡啶基烷基醇的衍生物可用作磷酸二酯酶4（PDE4）的抑制剂，用于治疗慢性阻塞性肺疾病等某些疾病。
• A Sulfonamide Sialoside Analogue for Targeting Siglec-8 and -F on Immune Cells
  作者：Corwin M. Nycholat、Shiteng Duan、Eva Knuplez、Charli Worth、Mila Elich、Anzhi Yao、Jeremy O’Sullivan、Ryan McBride、Yadong Wei、Steve M. Fernandes、Zhou Zhu、Ronald L. Schnaar、Bruce S. Bochner、James C. Paulson

  DOI：10.1021/jacs.9b05769

  日期：2019.9.11

  im-munoglobulin-like cell surface receptors have emerged as attractive targets for cell directed therapies due to their restricted expression on immune cells, endocytic properties and ability to modulate receptor signaling. Human Siglec-8, for instance has been identified as a therapeutic target for the treatment of eosinophil and mast cell disorders. A promising strategy to target Sig-lecs involves the

  Siglec 家族的唾液酸结合免疫球蛋白样细胞表面受体已成为细胞定向治疗的有吸引力的靶点，因为它们在免疫细胞上的表达受限、内吞特性和调节受体信号的能力。例如，人类 Siglec-8 已被确定为治疗嗜酸性粒细胞和肥大细胞疾病的治疗靶点。靶向 Sig-lecs 的一个有前景的策略涉及使用具有多价展示 Siglec 配体的脂质体纳米颗粒。这种方法的一个关键挑战是识别目标 Siglec 的高亲和力配体。在这里，我们报告了 Siglec-8 的高亲和力配体及其最接近的鼠功能直向同源物 Siglec-F 的开发，它能够将脂质体靶向表达 Siglec-8 或 -F 的细胞。筛选了 156 个合成的 9-N-磺酰基唾液酸类似物的聚糖微阵列库，以识别潜在的先导化合物。最佳配体，9-N-(2-萘基磺酰基)-Neu5Acα2-3-[6-O-磺基]-Galβ1-4GlcNAc(6'-O-磺基NSANeu5Ac)结