4-（吡啶-3-基甲氧基）苯甲醛 | 118001-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-（吡啶-3-基甲氧基）苯甲醛
• 英文名称: 4-[(pyridin-3-yl)-methyloxy]-benzaldehyde
• 英文别名: 4-(pyridin-3-ylmethoxy)-benzaldehyde；4-(pyridin-3-ylmethoxy)benzaldehyde；4-[(3-pyridyl)-methyloxy]-benzaldehyde；4-(3-pyridylmethoxy)benzaldehyde
• CAS: 118001-72-2
• 化学式: C₁₃H₁₁NO₂
• mdl: MFCD03069519
• 分子量: 213.236
• InChiKey: OZLAHUVAOGTVKY-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C(Solv: ethanol (64-17-5))
• 沸点：
  395.7±22.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-(Pyridin-3-ylmethoxy)benzaldehyde
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-(Pyridin-3-ylmethoxy)benzaldehyde
CAS number: 118001-72-2

---

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: C13H11NO2
Molecular weight: 213.2

---

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.

---

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：

  4-（吡啶-3-基甲氧基）苯甲醛 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 5-(4-hydroxyphenyl)dipyrrin
  参考文献：
  名称：

  DNA Binding and Anti-Cancer Activity of Redox-Active Heteroleptic Piano-Stool Ru(II), Rh(III), and Ir(III) Complexes Containing 4-(2-Methoxypyridyl)phenyldipyrromethene

  摘要：

  The synthesis of four novel heteroleptic dipyrrinato complexes [(eta(6)-arene)RuCl(2-pcdpm)] (eta(6)-arene = C6H6, 1; C10H14, 2) and [(eta(5)-C5Me5)MCl(2-pcdpm)] (M = Rh, 3; Ir, 4) containing a new chelating ligand 4-(2-methoxypyridyl)-phenyldipyrromethene (2-pcdpm) have been described. The complexes 1-4 have been fully characterized by various physicochemical techniques, namely, elemental analyses, spectral (ESI-MS, IR, H-1, C-13 NMR, UV/vis) and electrochemical studies (cyclic voltammetry (CV) and differential pulse voltammetry (DPV)). Structures of 3 and 4 have been determined crystallographically. In vitro antiproliferative and cytotoxic activity of these complexes has been evaluated by trypan blue exclusion assay, cell morphology, apoptosis, acridine orange/ethidium bromide (AO/EtBr) fluorescence staining, and DNA fragmentation assay in Dalton lymphoma (DL) cell lines. Interaction of 1-4 with calf thymus DNA (CT DNA) has also been supported by absorption titration and electrochemical studies. Our results suggest that in vitro antitumor activity of 1-4 lies in the order 2 > 1 > 4 > 3.

  DOI：

  10.1021/ic302196v
• 作为产物：
  描述：

  3-吡啶甲醇 、 对羟基苯甲醛 在 偶氮二甲酸二苄酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 4-（吡啶-3-基甲氧基）苯甲醛
  参考文献：
  名称：

  3-Benzyl-1,3-oxazolidin-2-ones as mGluR2 positive allosteric modulators: Hit-to lead and lead optimization

  摘要：

  The discovery, synthesis and SAR of a novel series of 3-benzyl-1,3-oxazolidin-2-ones as positive allosteric modulators (PAMs) of mGluR2 is described. Expedient hit-to-lead work on a single HTS hit led to the identification of a ligand-efficient and structurally attractive series of mGluR2 PAMs. Human microsomal clearance and suboptimal physicochemical properties of the initial lead were improved to give potent, metabolically stable and orally available mGluR2 PAMs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.032

文献信息

• Histidine-(N-benzyl glycinamide) inhibitors of protein farnesyl transferase
  申请人：Warner-Lambert Company

  公开号：US06300501B1

  公开（公告）日：2001-10-09

  Inhibitors of protein farnesyl transferase enzymes are described, as well as methods for the preparation and pharmaceutical compositions of the same, which are useful in treating cancer, restenosis, psoriasis, endometriosis, atherosclerosis, or viral infections.

  蛋白质法尼基转移酶酶的抑制剂被描述，以及用于制备和药物组合物的方法，这些方法在治疗癌症、再狭窄、银屑病、子宫内膜异位症、动脉粥样硬化或病毒感染方面是有用的。
• Preparation of 2-aryl and 2-aryloxymethyl imidazo[1,2-<i>a</i>]pyridines and related compounds
  作者：Richard J. Sundberg、D. J. Dahlhausen、G. Manikumar、B. Mavunkel、Atanu Biswas、V. Srinivasan、Fred King、Philip Waid

  DOI：10.1002/jhet.5570250119

  日期：1988.1

  A series of substituted 2-aryl imidazo[1,2-a]pyridines has been prepared in which a variety of substituents are introduced on the 4′-position of the phenyl ring and on the 3, 5, 6 or 7 position of the heterocyclic ring. Most examples have acetamido, bromo, cyano, or formyl substituents at the 4′-position. Analogous imidazo-[2,1-b]fhiazoles and imidazo[1,2-a]pyrimidines have also been prepared. Another

  一系列取代的2-芳基咪唑并[1,2-α]吡啶已被制备，其中多种取代基被引入在苯环的4'位和在3，5的，6或7位杂环。大多数实例在4'-位具有乙酰氨基，溴，氰基或甲酰基取代基。还已经制备了类似的咪唑并[ 2，1- b ]噻唑和咪唑并[1,2- a ]嘧啶。制备了由咪唑的4'-甲酰基苯氧基甲基衍生物，吡啶，噻唑，苯并咪唑和环取代的咪唑并[1,2- a ]吡啶的三个位置异构体组成的另一系列化合物。还制备了咪唑和咪唑并[1,2- a ]吡啶的2-（4'-甲酰基苯基乙烯基）衍生物。
• Isoxazol-5(4H)one Derivatives as PTP1B Inhibitors Showing an Anti-Obesity Effect
  作者：Bhooshan Kafle、Nilkanth G. Aher、Deegendra Khadka、Hwangseo Park、Hyeongjin Cho

  DOI：10.1002/asia.201100154

  日期：2011.8.1

  prepared in a day by using the present protocol. The library compounds thus obtained were examined for their inhibitory activities against PTP1B. Among them, compound C3 was the most potent inhibitor of PTP1B with an IC50 of 2.3 μM. The in vivo effect of C3 was also examined in an obesity‐prone mouse strain. Diet‐induced obese (DIO)/diabetic mice were divided into two groups and each group was fed a

  在开发治疗性目标酶的抑制剂中，大量的时间和精力致力于大量化合物的制备。为了开发一种有效的蛋白酪氨酸磷酸酶（PTP）1B抑制剂作为抗肥胖和/或抗糖尿病药，我们使用简化的程序构建了一个异恶唑酮化学库，该程序避免了繁琐的后处理和纯化步骤。10×7异恶唑酮衍生物是通过将两半目标化合物偶联而合成的。当在试管中混合并加热时，前体产生的反应产物为沉淀物。短暂洗涤后，产物纯度足以用于酶促实验。通过制备用于偶联反应的前体，可以使用本方案在一天之内制备10×7库化合物。检查由此获得的文库化合物对PTP1B的抑制活性。其中，复合C3是PTP1B的最有效的抑制剂，其IC 50为2.3μ中号。还对易肥胖的小鼠品系中的C3进行了体内研究。饮食诱导的肥胖（DIO）/糖尿病小鼠分为两组，每组喂养高脂饮食（HFD）或HFD + C3，持续4周。与喂食HFD的对照组相比，在喂食期的四个星期内，C3喂食的小鼠组的体重显着减少。
• Rational Design and Synthesis of 4-O-Substituted Phenylmethylenethiosemicarbazones as Novel Tyrosinase Inhibitors
  作者：Wei Yi、Rihui Cao、Zhiyong Chen、Liang Yu、Huan Wen、Qin Yan、Lin Ma、Huacan Song

  DOI：10.1248/cpb.58.752

  日期：——

  In continuing our program aimed to search for tyrosinase inhibitors, a series of novel 4-O-substituted phenylmethylenethiosemicarbazones were rational designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were also evaluated. A fair number of compounds were found to have significant tyrosinase inhibitiory activity. Particularly, the IC50 values of compounds 3a—g, 3j and 3s were of the same magnitude as tropolone, one of the best tyrosinase inhibitors known so far. Furthermore, the structure–activity relationships of these compounds were also investigated. All these data suggested that these molecules might be utilized for the development of new candidate for the treatment of dermatological disorders, and further development of such compounds may be of interest.

  在我们继续进行寻找酪氨酸酶抑制剂的项目中，合理设计并合成了一系列新型的4-O取代苯甲烯硫脲衍生物，同时评估了它们对蘑菇酪氨酸酶二酚酶活性的抑制效果。发现相当多的化合物具有显著的酪氨酸酶抑制活性。特别是化合物3a—g、3j和3s的IC50值与已知的最佳酪氨酸酶抑制剂之一的特罗泊酮相当。此外，这些化合物的结构—活性关系也进行了研究。所有这些数据表明，这些分子可能被用于开发治疗皮肤疾病的新候选药物，而且对这些化合物的进一步开发可能会引起兴趣。
• Inhibitors of matrix metalloproteinases
  申请人：Ferdinandy Péter

  公开号：US09487462B2

  公开（公告）日：2016-11-08

  Compounds of general formula (I), salts or solvates thereof and pharmaceutical compositions containing same: wherein Z is N or CH or the Z(R1) part is replaced with a covalent bond, m and n is 0, 1, 2 or 3; HET is heteroaryl; X is CF3, halogen, CO-heterocyclyl, COOR3 or CONHR3; R1 is H, (CH2)o-aryl, (CH2)p-heteroaryl, (CH2)q-biphenyl; C(O)—R5; S(O)2—R6; R2 is H, aryl, heteroaryl, Y—(CH2)r-aryl, Y—(CH2)s-heteroaryl, where some of the above substituents may be substituted; Y is O or S; with the exclusion of the compound where HET is 1,3-thiazol, X is COOH, R1 is 4-fluorophenyl and R2 is benzyloxy. The invention also relates to the use of a compound of general formula (I), salts or solvates thereof for the use in the prevention or treatment of diseases where the activation of MMPs is involved in the pathomechanism. In this aspect the use of the above excluded compound is also inventive.

  通式（I）化合物、其盐或溶剂化合物以及含有这些化合物的药物组合物：其中Z为N或CH，或Z（R1）部分被共价键替换，m和n为0、1、2或3；HET为杂环芳基；X为CF3、卤素、CO-杂环烷基、COOR3或CONHR3；R1为H、（CH2）o-芳基、（CH2）p-杂环芳基、（CH2）q-联苯基；C（O）—R5；S（O）2—R6；R2为H、芳基、杂环芳基、Y—（CH2）r-芳基、Y—（CH2）s-杂环芳基，其中上述取代基中的一些可能被取代；Y为O或S；不包括HET为1,3-噻唑、X为COOH、R1为4-氟苯基和R2为苄氧基的化合物。该发明还涉及使用通式（I）化合物、其盐或溶剂化合物用于预防或治疗MMPs激活参与病理机制的疾病。在这方面，上述排除的化合物的使用也是创新的。