4-苯基烟酸 | 103863-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-苯基烟酸
• 英文名称: 4-phenylpyridine-3-carboxylic acid
• 英文别名: 4-phenylnicotinic acid；4-Phenylpyridin-3-carbonsaeure；4-phenyl-3-pyridinecarboxylic acid
• CAS: 103863-14-5
• 化学式: C₁₂H₉NO₂
• mdl: MFCD04114252
• 分子量: 199.209
• InChiKey: HMFLWFBUKXQGIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  353.7±22.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Phenylnicotinic acid
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: 4-Phenylnicotinic acid
CAS number: 103863-14-5

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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: C12H9NO2
Molecular weight: 199.2

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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.

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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：

  4-苯基烟酸 在 盐酸 、 PPA 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-aza-9-hydroxy-9-fluorene carboxylic acid methyl ester
  参考文献：
  名称：

  9-Hydroxyazafluorenes and Their Use in Thrombin Inhibitors

  摘要：

  Optimization of a previously reported thrombin inhibitor, 9-hydroxy-9-fluorenylcarbonyl-l-prolyl-trans-4-aminocyclohexylmethylamide (1), by replacing the aminocyclohexyl P1 group provided a new lead structure, 9-hydroxy-9-fluorenylcarbonyl-l-prolyl-2-aminomethyl-5-chlorobenzylamide (2), with improved potency (K(i) = 0.49 nM for human thrombin, 2x APTT = 0.37 microM in human plasma) and pharmacokinetic properties (F = 39%, iv T(1/2) = 13 h in dogs). An effective strategy for reducing plasma protein binding of 2 and improving efficacy in an in vivo thrombosis model in rats was to replace the lipophilic fluorenyl group in P3 with an azafluorenyl group. Systematic investigation of all possible azafluorenyl P3 isomers and azafluorenyl-N-oxide analogues of 2 led to the identification of an optimal compound, 3-aza-9-hydroxyfluoren-9(R)-ylcarbonyl-l-prolyl-2-aminomethyl-5-chlorobenzylamide (19b), with high potency (K(i) = 0.40 nM, 2x APTT = 0.18 microM), excellent pharmacokinetic properties (F = 55%, T(1/2) = 14 h in dogs), and complete efficacy in the in vivo thrombosis model in rats (inhibition of FeCl(3)-induced vessel occlusions in six of six rats receiving an intravenous infusion of 10 microg/kg/min of 19b). The stereochemistry of the azafluorenyl group in 19b was determined by X-ray crystallographic analysis of its N-oxide derivative (23b) bound in the active site of human thrombin.

  DOI：

  10.1021/jm049423s
• 作为产物：
  描述：

  4-phenylpyridine-3-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-苯基烟酸
  参考文献：
  名称：

  9-Hydroxyazafluorenes and Their Use in Thrombin Inhibitors

  摘要：

  Optimization of a previously reported thrombin inhibitor, 9-hydroxy-9-fluorenylcarbonyl-l-prolyl-trans-4-aminocyclohexylmethylamide (1), by replacing the aminocyclohexyl P1 group provided a new lead structure, 9-hydroxy-9-fluorenylcarbonyl-l-prolyl-2-aminomethyl-5-chlorobenzylamide (2), with improved potency (K(i) = 0.49 nM for human thrombin, 2x APTT = 0.37 microM in human plasma) and pharmacokinetic properties (F = 39%, iv T(1/2) = 13 h in dogs). An effective strategy for reducing plasma protein binding of 2 and improving efficacy in an in vivo thrombosis model in rats was to replace the lipophilic fluorenyl group in P3 with an azafluorenyl group. Systematic investigation of all possible azafluorenyl P3 isomers and azafluorenyl-N-oxide analogues of 2 led to the identification of an optimal compound, 3-aza-9-hydroxyfluoren-9(R)-ylcarbonyl-l-prolyl-2-aminomethyl-5-chlorobenzylamide (19b), with high potency (K(i) = 0.40 nM, 2x APTT = 0.18 microM), excellent pharmacokinetic properties (F = 55%, T(1/2) = 14 h in dogs), and complete efficacy in the in vivo thrombosis model in rats (inhibition of FeCl(3)-induced vessel occlusions in six of six rats receiving an intravenous infusion of 10 microg/kg/min of 19b). The stereochemistry of the azafluorenyl group in 19b was determined by X-ray crystallographic analysis of its N-oxide derivative (23b) bound in the active site of human thrombin.

  DOI：

  10.1021/jm049423s

文献信息

• Thrombin inhibitors
  申请人：——

  公开号：US20020119992A1

  公开（公告）日：2002-08-29

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: 1 or a pharmaceutically acceptable salt thereof, e.g. where R 3 is —CH 2 NH 2 , —CH 2 CH 2 NH 2 , or —CH 2 NHC(O)OC(CH 3 ) 3 .

  该发明的化合物在抑制凝血酶和相关血栓闭塞方面具有以下结构： 1 或其药用可接受的盐，例如其中R 3 为—CH 2 NH 2 ，—CH 2 CH 2 NH 2 ，或—CH 2 NHC(O)OC(CH 3 ) 3 。
• [EN] VOLTAGE-GATED SODIUM CHANNEL BLOCKERS<br/>[FR] BLOQUEURS DES CANAUX SODIQUES VOLTAGE-DÉPENDANTS
  申请人：GLAXO GROUP LTD

  公开号：WO2013006596A1

  公开（公告）日：2013-01-10

  In general, the present invention relates to uses of voltage-gated sodium channel blocker compounds,, which include corresponding precursors, intermediates, monomers and dimers, corresponding pharmaceutical compositions, compound preparation and treatment methods for respiratory and respiratory tract diseases. In particular, the present invention also relates to methods and uses for treatment of respiratory or respiratory tract diseases, which comprises administering to a subject in need thereof an effective amount of a compound of the present invention.

  一般而言，本发明涉及使用电压门控钠通道阻滞剂化合物，包括相应的前体、中间体、单体和二聚体，相应的药物组合物，化合物制备和治疗方法，用于呼吸和呼吸道疾病。具体而言，本发明还涉及用于治疗呼吸或呼吸道疾病的方法和用途，包括向需要的受试者施用本发明化合物的有效量。
• A sustainable heterogenized palladium catalyst for Suzuki-Miyaura cross coupling reaction of azaheteroaryl halides in aqueous media
  作者：S. Ganesamoorthy、M. Muthu Tamizh、K. Shanmugasundaram、R. Karvembu

  DOI：10.1016/j.jorganchem.2018.02.030

  日期：2018.5

  A unique recyclable Pd catalyst (‘SiO2’-NH2-Pd) for Suzuki-Miyaura coupling reaction of azaheteroaryl halides is developed. The catalytic system is working under mild aqueous condition with low Pd loading and without the use of phosphine ligand. The plausible mechanism is proposed based on the formation of undesired symmetrical biaryl from the coupling reaction of azaheteroaryl chlorides due to the

  一个独特的可回收的Pd催化剂（“的SiO 2 ” -NH 2为azaheteroaryl卤化物的铃木-宫浦偶合反应-Pd）被显影。催化系统在温和的水性条件下工作，Pd含量低，并且不使用膦配体。基于亲核芳基硼酸的氧化均偶联，由氮杂杂芳基氯的偶合反应形成不希望的对称联芳基，提出了可能的机理。该催化体系代表了具有高产率的合成氮杂杂联芳基的有吸引力且有希望的方法。该催化剂显示出优异的可回收性。
• Nitrogen introduction of spirobifluorene to form α-, β-, γ-, and δ-aza-9,9′-spirobifluorenes: New bipolar system for efficient blue organic light-emitting diodes
  作者：Peng Wu、Jun Zhu、Zhen Zhang、Dehai Dou、Hedan Wang、Bin Wei、Zixing Wang

  DOI：10.1016/j.dyepig.2018.03.066

  日期：2018.9

  γ-aza-SBF and δ-aza-SBF showed overlapped HOMO and LUMO orbitals. The aza-SBFs showed excellent bipolar features and good thermal stabilities than those of SBFs. The maximum current efficiencies (CE) of α-, β-, γ-, and δ-aza-SBF-based OLEDs were 28.8, 24.9, 25.5, and 27.2 cd/A, respectively. Compared to the SBF, all of four aza-SBFs showed better devices performances. The CE and power efficiency (PE) of OLED

  合成了四个在一个芴部分的不同位置带有氮原子的aza-9,9'-spirbibifluorenes（aza-SBFs），以研究其结构性质之间的关系。α-Aza-SBF和β-aza-SBF几乎完全分开了最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO），而γ-aza-SBF和δ-aza-SBF显示出HOMO和LUMO重叠轨道。氮杂-SBF比SBF表现出优异的双极性特性和良好的热稳定性。α-，β-，γ-和δ-aza-SBF的最大电流效率（CE）的OLED分别为28.8、24.9、25.5和27.2 cd / A。与SBF相比，所有四个aza-SBF均显示出更好的器件性能。基于α-氮杂-SBF的OLED的CE和功率效率（PE）为28.8 cd / A和22.6 lm / W，而基于SBF的OLED仅为12.3 cd / A和8.2 lm / W。基于氮-氮杂-SBF的OLED的最大外部量子效率为15
• Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release
  作者：Pooja Jain、James T. Slama、LeRoy A. Perez-Haddock、Timothy F. Walseth

  DOI：10.1021/jm1007209

  日期：2010.11.11

  in potency for competition ligand binding assays using [32P]NAADP. In contrast, several 5-substituted NAADP derivatives showed high potency for binding and full agonist activity for Ca2+ release. 5-Azido-NAADP was shown to release calcium from sea urchin egg homogenates at low concentration and to compete with [32P]NAADP in a competition ligand binding assay with an IC50 of 18 nM, indicating that this

  在烟酸部分的 4 位或 5 位位置被取代的烟酸腺嘌呤二核苷酸磷酸 (NAADP) 的类似物已使用Aplysia californica ADP-核糖基环化酶或哺乳动物 NAD 糖水解酶从 NADP 酶促合成。烟酸的 4 位取代导致从海胆卵匀浆中释放 Ca 2+ 离子的激动剂效力丧失，并导致使用 [ 32 P]NAADP进行竞争配体结合测定的效力丧失。相比之下，几种 5-取代 NAADP 衍生物显示出对 Ca 2+ 的高结合力和完全激动剂活性释放。5-叠氮基-NAADP 以低浓度从海胆卵匀浆中释放钙，并在竞争配体结合试验中与[ 32 P]NAADP 竞争，IC 50为 18 nM，表明该化合物可能是一种潜在的光探针可用于 NAADP 受体的特异性标记和鉴定。