2-甲基-5-(吗啉-4-磺酰基)-苯胺 | 21447-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-5-(吗啉-4-磺酰基)-苯胺
• 英文名称: 3-Amino-4-methyl-benzolsulfonsaeure-morpholid
• 英文别名: 4-(3-amino-4-methyl-benzenesulfonyl)-morpholine；2-Methyl-5-(morpholine-4-sulfonyl)-phenylamine；2-methyl-5-morpholin-4-ylsulfonylaniline
• CAS: 21447-56-3
• 化学式: C₁₁H₁₆N₂O₃S
• mdl: MFCD02701332
• 分子量: 256.326
• InChiKey: OGFHXMSWYWAUDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  81
• 氢给体数：
  1
• 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: 2-Methyl-5-(morpholine-4-sulfonyl)-phenylamine
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: 2-Methyl-5-(morpholine-4-sulfonyl)-phenylamine
CAS number: 21447-56-3

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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: C11H16N2O3S
Molecular weight: 256.3

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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：

  2-甲基-5-(吗啉-4-磺酰基)-苯胺 在 吡啶 、 盐酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  人组织蛋白酶D小分子抑制剂的鉴定及构效关系研究

  摘要：

  组织蛋白酶 D 是一种天冬氨酰蛋白酶，是多种疾病（主要是癌症和骨关节炎）的有吸引力的治疗靶点。然而，尽管正在开发几种小分子组织蛋白酶 D 抑制剂，它们非常有效，但其中大多数表现出较差的微粒体稳定性，这反过来限制了它们的临床转化。在此，我们描述了一系列基于组织蛋白酶 D 的新型非肽酰基胍小分子抑制剂的设计、优化和评估。我们命中化合物1a（IC 50  = 29 nM）的优化导致了高效的单磺酰胺类似物4b（集成电路50 = 4 nM)，但微粒体稳定性较差（HLM：177 和 MLM：177 μl/min/mg）。为了在保留效力的同时进一步提高微粒体稳定性，我们进行了广泛的构效关系筛选，从而确定了我们优化的先导24e (IC 50  = 45 nM)，并提高了微粒体稳定性（HLM：59.1 和 MLM ：86.8 微升/分钟/毫克）。我们的努力表明，24e可能是针对组织蛋白酶 D 起重要作用的疾

  DOI：

  10.1016/j.bmc.2020.115879
• 作为产物：
  描述：

  4-(4-methyl-3-nitrophenylsulfonyl)morpholine 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 生成 2-甲基-5-(吗啉-4-磺酰基)-苯胺
  参考文献：
  名称：

  潜在的抗癌药。V.与3- [N，N-双（2-氯乙基）氨基] -4-甲基苯甲酸有关的新的芳香氮芥。

  摘要：

  DOI：

  10.1021/jm00301a043

文献信息

• Synthesis of 5-enamine-4-thiazolidinone derivatives with trypanocidal and anticancer activity
  作者：Serhii Holota、Anna Kryshchyshyn、Halyna Derkach、Yaroslava Trufin、Inna Demchuk、Andrzej Gzella、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.bioorg.2019.01.045

  日期：2019.5

  DTP protocol allowed to identify active 2-(5-[5-(2,4-dichlorobenzyl)-thiazol-2-ylamino]-methylene}-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropionic acid ethyl ester 14 that demonstrated inhibition against all 59 human tumor cell lines with the average GI50 value of 2.57 μM. It was established that the activity type (antitrypanosomal or anticancer) as well as its level depends on the character of enamine

  合成了一系列新颖的2-（5-氨基亚甲基-4-氧代-2-硫代噻唑并恶唑烷-3-基）-3-苯基丙酸乙酯。评价靶标化合物对布鲁氏锥虫和冈比亚锥虫的锥虫杀虫活性。几种命中化合物（8、10、12）在亚微摩尔浓度（IC50 0.027-1.936 µM）下抑制了寄生虫的生长，并显示出对人类原代成纤维细胞无毒的显着选择性指数（SI = 108-1396.2）。在NCI DTP方案中对体外抗癌活性的筛选可以鉴定出活性的2-（5-[5-（2,4-二氯苄基）-噻唑-2-基氨基]-亚甲基} -4-氧代-2-硫代噻唑烷- 3-yl）-3-苯基丙酸乙酯14表现出对所有59种人类肿瘤细胞系的抑制作用，平均GI50值为2.57μM。
• Potential anticancer agents. V. Aromatic nitrogen mustards related to 3-[N,N-bis(2-chloroethyl)amino]-4-methylbenzoic acid
  作者：A. Cambanis、V. Dobre、Ion Niculescu-Duvaz

  DOI：10.1021/jm00301a043

  日期：1969.1
• Identification and structure-activity relationship studies of small molecule inhibitors of the human cathepsin D
  作者：Sandeep Goyal、Ketul V. Patel、Yadav Nagare、Digambar B. Raykar、Santosh S. Raikar、Atul Dolas、Princy Khurana、Rajath Cyriac、Sharad Sarak、Mukesh Gangar、Anil K. Agarwal、Aditya Kulkarni

  DOI：10.1016/j.bmc.2020.115879

  日期：2021.1

  Cathepsin D, an aspartyl protease, is an attractive therapeutic target for various diseases, primarily cancer and osteoarthritis. However, despite several small molecule cathepsin D inhibitors being developed, that are highly potent, most of them show poor microsomal stability, which in turn limits their clinical translation. Herein, we describe the design, optimization and evaluation of a series of

  组织蛋白酶 D 是一种天冬氨酰蛋白酶，是多种疾病（主要是癌症和骨关节炎）的有吸引力的治疗靶点。然而，尽管正在开发几种小分子组织蛋白酶 D 抑制剂，它们非常有效，但其中大多数表现出较差的微粒体稳定性，这反过来限制了它们的临床转化。在此，我们描述了一系列基于组织蛋白酶 D 的新型非肽酰基胍小分子抑制剂的设计、优化和评估。我们命中化合物1a（IC 50  = 29 nM）的优化导致了高效的单磺酰胺类似物4b（集成电路50 = 4 nM)，但微粒体稳定性较差（HLM：177 和 MLM：177 μl/min/mg）。为了在保留效力的同时进一步提高微粒体稳定性，我们进行了广泛的构效关系筛选，从而确定了我们优化的先导24e (IC 50  = 45 nM)，并提高了微粒体稳定性（HLM：59.1 和 MLM ：86.8 微升/分钟/毫克）。我们的努力表明，24e可能是针对组织蛋白酶 D 起重要作用的疾