6-溴-1-苯基磺酰基-1H-吲哚 | 679794-03-7

• 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: 6-溴-1-苯基磺酰基-1H-吲哚
• 英文名称: 6-bromo-1-(phenylsulfonyl)-1H-indole
• 英文别名: 1-(benzenesulfonyl)-6-bromoindole
• CAS: 679794-03-7
• 化学式: C₁₄H₁₀BrNO₂S
• 分子量: 336.209
• InChiKey: NENPDYQYNRFWQU-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C(Solv: methanol (67-56-1))
• 沸点：
  498.0±37.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-1-(phenylsulfonyl)-1H-indole
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: 6-Bromo-1-(phenylsulfonyl)-1H-indole
CAS number: 679794-03-7

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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.
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: C14H10BrNO2S
Molecular weight: 336.2

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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, hydrogen bromide, 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：

  6-溴-1-苯基磺酰基-1H-吲哚 在 lithium diisopropyl amide 、 1,2-二碘乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.42h， 以53%的产率得到6-bromo-2-iodo-1-(phenylsulfonyl)-1H-indole
  参考文献：
  名称：

  Discovery and optimization of a new class of pyruvate kinase inhibitors as potential therapeutics for the treatment of methicillin-resistant Staphylococcus aureus infections

  摘要：

  A novel series of bis-indoles derived from naturally occurring marine alkaloid 4 were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK is not only critical for bacterial survival which would make it a target for development of novel antibiotics, but it is reported to be one of the most highly connected 'hub proteins' in MRSA, and thus should be very sensitive to mutations and making it difficult for the bacteria to develop resistance. From the co-crystal structure of cis-3-4-dihydrohamacanthin B (4) bound to S. aureus PK we were able to identify the pharmacophore needed for activity. Consequently, we prepared simple direct linked bis-indoles such as 10b that have similar anti-MRSA activity as compound 4. Structure-activity relationship (SAR) studies were carried out on 10b and led us to discover more potent compounds such as 10c, 10d, 10k and 10m with enzyme inhibiting activities in the low nanomolar range that effectively inhibited the bacteria growth in culture with minimum inhibitory concentrations (MIC) for MRSA as low as 0.5 mu g/ml. Some potent PK inhibitors, such as 10b, exhibited attenuated antibacterial activity and were found to be substrates for an efflux mechanism in S. aureus. Studies comparing a wild type S. aureus with a construct (S. aureus LAC Delta pyk::ErmR) that lacks PK activity confirmed that bactericidal activity of 10d was PK-dependant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.020
• 作为产物：
  描述：

  β-dimethylamino-2-nitrostyrene 在 氢气 、 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 苯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 29.17h， 生成 6-溴-1-苯基磺酰基-1H-吲哚
  参考文献：
  名称：

  关于6-溴色胺的制备

  摘要：

  海洋天然产物6-溴色胺的大多数先前合成几乎可以肯定地导致部分脱溴，从而导致不纯的产物含有色胺。我们表明，当在最终反应步骤中使用氢化铝锂作为还原剂时，会发生溴的损失，从而导致6-溴色胺。在6-溴吲哚（6-溴色胺的典型前体）的某些合成过程中，还原脱溴作用也很可能进入。所描述的涉及6-溴吲哚还原序列的6-溴色胺的七种合成方法均未报道将元素分析作为纯度的量度。

  DOI：

  10.1016/j.tet.2021.132055

文献信息

• [EN] ANTI-BACTERIAL PYRUVATE KINASE MODULATOR COMPOUNDS, COMPOSITIONS, USES, AND METHODS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS MODULATEURS DE LA PYRUVATE KINASE, COMPOSITIONS, UTILISATIONS ET MÉTHODES ASSOCIÉES
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2012051708A1

  公开（公告）日：2012-04-26

  Compounds having a structure of Formulas A-C are provided. Uses of such compounds as an antibiotic, including both gram-negative and gram-positive micro-organisms, as well as methods of treatment and uses involving such compounds are provided.

  提供了具有A-C式结构的化合物。提供了这些化合物作为抗生素的用途，包括革兰氏阴性和革兰氏阳性微生物，以及涉及这些化合物的治疗方法和用途。
• [EN] MACROCYCLIC INHIBITORS OF PEPTIDYLARGININE DEIMINASES<br/>[FR] INHIBITEURS MACROCYCLIQUES DE PEPTIDYLARGININE DÉIMINASES
  申请人：GILEAD SCIENCES INC

  公开号：WO2021222353A1

  公开（公告）日：2021-11-04

  The present disclosure relates to novel compounds for use in therapeutic treatement of a disease associated with peptidylarginine deiminases (PADs), such as peptidylarginine deiminase type 4 (PAD4). The present disclosure also relates to processes and intermediates for the preparation of such compounds, methods of using such compounds and pharmaceutical compositions comprising the compounds described herein.

  本公开涉及用于治疗与肽精氨酸脱亚氨酶（PADs）相关的疾病的新化合物，例如肽精氨酸脱亚氨酶类型4（PAD4）。本公开还涉及用于制备这些化合物的过程和中间体，使用这些化合物的方法以及包含所述化合物的药物组合物。
• Palladium-Catalyzed <i>anti</i>-Michael Reductive Heck Reaction of α,β-Unsaturated Esters
  作者：Tao Guo、Yalan Ding、Lili Zhou、Haiyan Xu、Teck-Peng Loh、Xiaojin Wu

  DOI：10.1021/acscatal.0c02414

  日期：2020.7.2

  A general intermolecular anti-Michael reductive Heck reaction of α,β-unsaturated esters with organobromides has been developed. Most topical classes of aryl, heteroaryl, and vinyl bromides were found to efficiently react with a variety of internal conjugated alkenes. This protocol set up a platform toward diverse α-arylated 1,6-dicarbonyl frameworks found in natural products and drugs, which are still

  已经开发出α，β-不饱和酯与有机溴化物的一般分子间抗Michael还原Heck反应。发现大多数局部类型的芳基，杂芳基和乙烯基溴化物可与多种内部共轭烯烃有效反应。该方案为天然产物和药物中发现的各种α-芳基化1,6-二羰基构架建立了平台，由于烯醇化的竞争选择性，它们仍然是传统α-芳基化方案中极具挑战性的目标。可移动的导向基团，克级反应和对复杂分子的修饰还证明了该抗-Michael还原性Heck反应是经典α-芳基化方法的有力补充策略。初步的机理研究与我们提出的机理设计是一致的。
• Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile
  作者：Tomasz Janosik、Hamid Shirani、Niklas Wahlström、Ilham Malky、Birgitta Stensland、Jan Bergman

  DOI：10.1016/j.tet.2005.11.062

  日期：2006.2

  The sulfonation of various 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile has been studied, leading to the development of a clean and operationally simple protocol allowing direct synthesis of the corresponding 1-phenylsulfonyl-1H-pyrrole-3-sulfonyl chlorides and 1-phenylsulfonyl-1H-indole-3-sulfonyl chlorides, respectively, both of which may

  已经研究了使用氯磺酸在乙腈中磺化各种1-苯基磺酰基-1 H-吡咯和1-苯基磺酰基-1 H-吲哚的方法，从而开发了一种清洁，操作简单的方法，可以直接合成相应的1-苯基磺酰基-1 H-吡咯-3-磺酰氯和1-苯基磺酰基-1 H-吲哚-3-磺酰氯，通过用氮亲核试剂处理，它们都可以容易地转化为各种磺酰胺衍生物。在温和的条件下可以有效和选择性地除去磺酰胺系列中的苯磺酰基或甲苯磺酰基。
• Construction of Oxepino[3,2‐ <i>b</i> ]indoles via [4+3] Annulation of 2‐Ylideneoxindoles with Crotonate‐Derived Sulfur Ylides
  作者：Xing‐Hai Fei、Yong‐Long Zhao、Fen‐Fen Yang、Xiang Guan、Zong‐Qin Li、Da‐Peng Wang、Meng Zhou、Yuan‐Yong Yang、Bin He

  DOI：10.1002/adsc.202001580

  日期：2021.6.21

  A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed. A series of oxepino[3,2-b]indoles were prepared in moderate to excellent yields (62-93%) under mild conditions. Moreover, the synthetic oxepino[3,2-b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds

  已经开发了 2-ylideneoxindoles 与巴豆酸盐衍生的硫叶立德的 [4+3] 环化。在温和的条件下，以中等至极好的收率 (62-93%) 制备了一系列 oxepino[3,2- b ] 吲哚。此外，合成的oxepino[3,2- b ]吲哚可以通过[2+1]环丙烷化进一步转化为更复杂的环丙[5,6]oxepino[3,2- b ]吲哚。此外，合成的化合物对K562和MCF-7细胞显示出一定的抗增殖活性，对这两种肿瘤细胞的IC 50值分别高达5.40±0.88 μM和18.41±0.50 μM。