5-氨基-2,N,N-三甲基-苯磺酰胺 | 6331-67-5

• 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: 5-氨基-2,N,N-三甲基-苯磺酰胺
• 英文名称: 5-amino-N,N,2-trimethylbenzenesulfonamide
• 英文别名: 5-Amino-2,N,N-trimethyl-benzenesulfonamide
• CAS: 6331-67-5
• 化学式: C₉H₁₄N₂O₂S
• mdl: MFCD02704401
• 分子量: 214.288
• InChiKey: SNBPDMLVDOVULQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  >32.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2935009090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-Amino-2,n,n-trimethyl-benzenesulfonamide
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Amino-2,n,n-trimethyl-benzenesulfonamide
CAS number: 6331-67-5

---

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.
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: C9H14N2O2S
Molecular weight: 214.3

---

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.

---

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-氨基-2,N,N-三甲基-苯磺酰胺 在 草酰氯 、 palladium on activated charcoal 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Optical control of neuronal activity using a light-operated GIRK channel opener (LOGO)

  摘要：

  我们描述了可开关光受体激动剂LOGO的研发过程，该激动剂在黑暗中激活GIRK通道，并在长波紫外线照射下迅速失活。LOGO可用于光学沉默离体海马神经元的动作电位放电，并在体内表现出活性，以光依赖方式控制斑马鱼幼体的运动能力。

  DOI：

  10.1039/c5sc04084a
• 作为产物：
  描述：

  2-甲基-5-硝基苯磺酰氯 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 5-氨基-2,N,N-三甲基-苯磺酰胺
  参考文献：
  名称：

  Optical control of neuronal activity using a light-operated GIRK channel opener (LOGO)

  摘要：

  我们描述了可开关光受体激动剂LOGO的研发过程，该激动剂在黑暗中激活GIRK通道，并在长波紫外线照射下迅速失活。LOGO可用于光学沉默离体海马神经元的动作电位放电，并在体内表现出活性，以光依赖方式控制斑马鱼幼体的运动能力。

  DOI：

  10.1039/c5sc04084a

文献信息

• Optical control of GIRK channels using visible light
  作者：Julie B. Trads、Jessica Burgstaller、Laura Laprell、David B. Konrad、Luis de la Osa de la Rosa、C. David Weaver、Herwig Baier、Dirk Trauner、David M. Barber

  DOI：10.1039/c6ob02153k

  日期：——

  G-protein coupled inwardly rectifying potassium (GIRK) channels are an integral part of inhibitory signal transduction pathways, reducing the activity of excitable cells via hyperpolarization. They play crucial roles in processes such as cardiac output, cognition and the coordination of movement. Therefore, the precision control of GIRK channels is of critical importance. Here, we describe the development

  G 蛋白偶联内向整流钾 (GIRK) 通道是抑制性信号转导通路的组成部分，通过超极化降低可兴奋细胞的活性。它们在心输出量、认知和运动协调等过程中起着至关重要的作用。因此，GIRK 通道的精确控制至关重要。在这里，我们描述了含有偶氮苯的分子VLOGO（可见光操作 GIRK 通道开启剂）的开发，它在黑暗中激活 GIRK 通道，并在用绿光照射时迅速停用。标志是对现有 GIRK 通道光学控制工具的宝贵补充，因为它避免了使用潜在有害紫外线照射的需要。因此，我们相信VLOGO将成为研究生物系统中 GIRK 通道的有用研究工具。
• Sign Inversion in Photopharmacology: Incorporation of Cyclic Azobenzenes in Photoswitchable Potassium Channel Blockers and Openers
  作者：Julie B. Trads、Katharina Hüll、Bryan S. Matsuura、Laura Laprell、Timm Fehrentz、Nicole Görldt、Krystian A. Kozek、C. David Weaver、Nikolaj Klöcker、David M. Barber、Dirk Trauner

  DOI：10.1002/anie.201905790

  日期：2019.10.21

  cis-form. Incorporation of these switches into a variety of photopharmaceuticals could convert dark-active ligands into dark-inactive ligands, which is preferred in most biological applications. This "pharmacological sign-inversion" is demonstrated for a photochromic blocker of voltage-gated potassium channels, termed CAL, and a photochromic opener of G protein-coupled inwardly rectifying potassium (GIRK)

  光药理学依赖于通过光异构化改变其药效学的配体。这些配体中的许多是偶氮苯，它们在延长的反式构型中在热力学上更稳定。通常，它们以这种形式具有生物活性，并且在辐射和光异构化为其顺式异构体时失去活性。最近，出现了环状偶氮苯，即所谓的重氮辛，它们的弯曲顺式形式在热力学上更稳定。将这些开关结合到各种光药物中可以将暗活性配体转化为暗活性配体，这在大多数生物应用中是首选。这种“药理学符号反转”被证明用于电压门控钾通道的光致变色阻滞剂，称为 CAL，
• Triazole compounds that modulate Hsp90 activity
  申请人：Sun Lijun

  公开号：US20080176840A1

  公开（公告）日：2008-07-24

  The present invention relates to substituted triazole compounds and compositions comprising substituted triazole compounds. The invention further relates to methods of inhibiting the activity of Hsp90 in a subject in need thereof and methods for preventing or treating hyperproliferative disorders, such as cancer, in a subject in need thereof comprising administering to the subject a substituted triazole compound of the invention, or a composition comprising such a compound.

  本发明涉及替代三唑化合物和包含替代三唑化合物的组合物。该发明还涉及在需要的受试者中抑制Hsp90活性的方法，以及预防或治疗过度增殖性疾病，如癌症，的方法，包括向受试者施用本发明的替代三唑化合物或包含这种化合物的组合物。
• Discovery of a First-in-Class Inhibitor of the PRMT5–Substrate Adaptor Interaction
  作者：David C. McKinney、Brian J. McMillan、Matthew J. Ranaghan、Jamie A. Moroco、Merissa Brousseau、Zachary Mullin-Bernstein、Meghan O’Keefe、Patrick McCarren、Michael F. Mesleh、Kathleen M. Mulvaney、Foxy Robinson、Ritu Singh、Besnik Bajrami、Florence F. Wagner、Robert Hilgraf、Martin J. Drysdale、Arthur J. Campbell、Adam Skepner、David E. Timm、Dale Porter、Virendar K. Kaushik、William R. Sellers、Alessandra Ianari

  DOI：10.1021/acs.jmedchem.1c00507

  日期：2021.8.12

  compound series which binds to the PRMT5–PBM interface and directly inhibits binding of SAPs. Mode of action studies revealed the formation of a covalent bond between a halogenated pyridazinone group and cysteine 278 of PRMT5. Optimization of the starting hit produced a lead compound, BRD0639, which engages the target in cells, disrupts PRMT5–RIOK1 complexes, and reduces substrate methylation. BRD0639

  PRMT5 及其底物衔接蛋白 (SAP) pICln 和 Riok1 在 MTAP 缺失的癌细胞中是合成的致死依赖性。SAP 共享一个保守的 PRMT5 结合基序 (PBM)，它介导与催化位点远端 PRMT5 表面的结合。这种相互作用是几种 PRMT5 底物甲基化所必需的，包括组蛋白和剪接体复合物。我们筛选了 PRMT5-PBM 相互作用的小分子抑制剂，并验证了与 PRMT5-PBM 界面结合并直接抑制 SAP 结合的化合物系列。作用模式研究揭示了在卤代哒嗪酮基团和 PRMT5 的半胱氨酸 278 之间形成共价键。对起始命中的优化产生了一种先导化合物 BRD0639，它使靶点进入细胞，破坏 PRMT5-RIOK1 复合物，并减少底物甲基化。
• Substituted Aminoacetamides as Novel Leads for Malaria Treatment
  作者：Neil R. Norcross、Caroline Wilson、Beatriz Baragaña、Irene Hallyburton、Maria Osuna‐Cabello、Suzanne Norval、Jennifer Riley、Daniel Fletcher、Robert Sinden、Michael Delves、Andrea Ruecker、Sandra Duffy、Stephan Meister、Yevgeniya Antonova‐Koch、Benigno Crespo、Cristina de Cózar、Laura M. Sanz、Francisco Javier Gamo、Vicky M. Avery、Julie A. Frearson、David W. Gray、Alan H. Fairlamb、Elizabeth A. Winzeler、David Waterson、Simon F. Campbell、Paul A. Willis、Kevin D. Read、Ian H. Gilbert

  DOI：10.1002/cmdc.201900329

  日期：2019.7.17

  Herein we describe the optimization of a phenotypic hit against Plasmodium falciparum based on an aminoacetamide scaffold. This led to N-(3-chloro-4-fluorophenyl)-2-methyl-2-[4-methyl-3-(morpholinosulfonyl)phenyl]amino}propanamide (compound 28) with low-nanomolar activity against the intraerythrocytic stages of the malaria parasite, and which was found to be inactive in a mammalian cell counter-screen

  在这里，我们描述了基于氨基乙酰胺支架的针对恶性疟原虫的表型命中的优化。这导致 N-(3-chloro-4-fluorophenyl)-2-methyl-2-[4-methyl-3-(morpholinosulfonyl)phenyl]amino}propanamide (compound 28) 对红细胞内阶段具有低纳摩尔活性疟原虫，在哺乳动物细胞反筛中发现其在高达 25 μm 的范围内无活性。双配子激活测定中配子的抑制表明该化合物家族也可能具有传输阻断能力。虽然我们无法将水溶性和微粒体稳定性优化到氨基乙酰胺适用于体内药代动力学和功效研究的程度，但化合物 28 显示出优异的抗疟效力和选择性；