1-TBDMS-吲哚-5-硼酸 | 913835-68-4

• 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-TBDMS-吲哚-5-硼酸
• 中文别名: 1-(叔丁基二甲基硅烷)吲哚-5-硼酸
• 英文名称: (1-(tert-butyldimethylsilyl)-1H-indol-5-yl)boronic acid
• 英文别名: 1-(tert-butyldimethylsilyl)-1H-indol-5-ylboronic acid；[1-[tert-butyl(dimethyl)silyl]indol-5-yl]boronic acid
• CAS: 913835-68-4
• 化学式: C₁₄H₂₂BNO₂Si
• 分子量: 275.231
• InChiKey: PPFZQIOBIOETAS-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250
• 沸点：
  352.1±48.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（轻微加热）、氯仿（轻微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501,P330,P361,P363,P391,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
1-TBDMS-indole-5-boronic acid
Product Name:
Synonyms: 1-TBDMS-5-indoleboronic acid; 1-(tert-Butyldimethylsilyl)-1H-indol-5-ylboronic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
1-TBDMS-indole-5-boronic acid
Ingredient name:
CAS number: 913835-68-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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, under −20◦C.
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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H22BNO2Si
Molecular weight: 275.2

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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：

  1-TBDMS-吲哚-5-硼酸 在 dipotassium hydrogenphosphate 、 四(三苯基膦)钯 、 四丁基氟化铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 5-(4-(1-(1H-imidazol-1-yl)allyl)phenyl)-1H-indole
  参考文献：
  名称：

  Structure‐Activity Relationship and Mode‐Of‐Action Studies Highlight 1‐(4‐Biphenylylmethyl)‐1 H ‐imidazole‐Derived Small Molecules as Potent CYP121 Inhibitors

  摘要：

  AbstractCYP121 of Mycobacterium tuberculosis (Mtb) is an essential target for the development of novel potent drugs against tuberculosis (TB). Besides known antifungal azoles, further compounds of the azole class were recently identified as CYP121 inhibitors with antimycobacterial activity. Herein, we report the screening of a similarity‐oriented library based on the former hit compound, the evaluation of affinity toward CYP121, and activity against M. bovis BCG. The results enabled a comprehensive SAR study, which was extended through the synthesis of promising compounds and led to the identification of favorable features for affinity and/or activity and hit compounds with 2.7‐fold improved potency. Mode of action studies show that the hit compounds inhibit substrate conversion and highlighted CYP121 as the main antimycobacterial target of our compounds. Exemplified complex crystal structures of CYP121 with three inhibitors reveal a common binding site. Engaging in both hydrophobic interactions as well as hydrogen bonding to the sixth iron ligand, our compounds block a solvent channel leading to the active site heme. Additionally, we report the first CYP inhibitors that are able to reduce the intracellular replication of M. bovis BCG in macrophages, emphasizing their potential as future drug candidates against TB.

  DOI：

  10.1002/cmdc.202100283
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.5h， 生成 1-TBDMS-吲哚-5-硼酸
  参考文献：
  名称：

  Structure‐Activity Relationship and Mode‐Of‐Action Studies Highlight 1‐(4‐Biphenylylmethyl)‐1 H ‐imidazole‐Derived Small Molecules as Potent CYP121 Inhibitors

  摘要：

  AbstractCYP121 of Mycobacterium tuberculosis (Mtb) is an essential target for the development of novel potent drugs against tuberculosis (TB). Besides known antifungal azoles, further compounds of the azole class were recently identified as CYP121 inhibitors with antimycobacterial activity. Herein, we report the screening of a similarity‐oriented library based on the former hit compound, the evaluation of affinity toward CYP121, and activity against M. bovis BCG. The results enabled a comprehensive SAR study, which was extended through the synthesis of promising compounds and led to the identification of favorable features for affinity and/or activity and hit compounds with 2.7‐fold improved potency. Mode of action studies show that the hit compounds inhibit substrate conversion and highlighted CYP121 as the main antimycobacterial target of our compounds. Exemplified complex crystal structures of CYP121 with three inhibitors reveal a common binding site. Engaging in both hydrophobic interactions as well as hydrogen bonding to the sixth iron ligand, our compounds block a solvent channel leading to the active site heme. Additionally, we report the first CYP inhibitors that are able to reduce the intracellular replication of M. bovis BCG in macrophages, emphasizing their potential as future drug candidates against TB.

  DOI：

  10.1002/cmdc.202100283

文献信息

• A Data-Driven Approach to the Development and Understanding of Chiroptical Sensors for Alcohols with Remote γ-Stereocenters
  作者：Jordan J. Dotson、Eric V. Anslyn、Matthew S. Sigman

  DOI：10.1021/jacs.1c09443

  日期：2021.11.17
• BRK INHIBITORY COMPOUND
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP3312182B9

  公开（公告）日：2022-06-29
• Structure‐Activity Relationship and Mode‐Of‐Action Studies Highlight 1‐(4‐Biphenylylmethyl)‐1 <i>H</i> ‐imidazole‐Derived Small Molecules as Potent CYP121 Inhibitors
  作者：Isabell Walter、Sebastian Adam、Maria Virginia Gentilini、Andreas M. Kany、Christian Brengel、Andreas Thomann、Tim Sparwasser、Jesko Köhnke、Rolf W. Hartmann

  DOI：10.1002/cmdc.202100283

  日期：2021.9.16

  AbstractCYP121 of Mycobacterium tuberculosis (Mtb) is an essential target for the development of novel potent drugs against tuberculosis (TB). Besides known antifungal azoles, further compounds of the azole class were recently identified as CYP121 inhibitors with antimycobacterial activity. Herein, we report the screening of a similarity‐oriented library based on the former hit compound, the evaluation of affinity toward CYP121, and activity against M. bovis BCG. The results enabled a comprehensive SAR study, which was extended through the synthesis of promising compounds and led to the identification of favorable features for affinity and/or activity and hit compounds with 2.7‐fold improved potency. Mode of action studies show that the hit compounds inhibit substrate conversion and highlighted CYP121 as the main antimycobacterial target of our compounds. Exemplified complex crystal structures of CYP121 with three inhibitors reveal a common binding site. Engaging in both hydrophobic interactions as well as hydrogen bonding to the sixth iron ligand, our compounds block a solvent channel leading to the active site heme. Additionally, we report the first CYP inhibitors that are able to reduce the intracellular replication of M. bovis BCG in macrophages, emphasizing their potential as future drug candidates against TB.