Tom ntej: 2-Bromo-3-pyridinecarboxaldehyde CAS 128071-75-0

2-Bromo-3-pyridinecarboxaldehyde (3-Pyridinecarboxaldehyde, 2-bromo-), tshuaj formula: C6H4BrNO, CAS 14533-22-9, molecular hnyav: 186.01 g/mol. Nws yog ib qho khoom, feem ntau nyob rau hauv daim ntawv ntawm ib tug dawb los yog yuav luag dawb crystalline hmoov. Nws muaj qee yam solubility hauv qee cov kuab tshuaj organic (xws li dichloromethane, ether, methanol, ethanol, thiab lwm yam). Txawm li cas los xij, thov nco ntsoov tias nws cov solubility yuav txawv nyob ntawm qhov kub, hnyav, thiab lwm yam. Raws li ib qho tseem ceeb organic compound, nws muaj ntau yam kev siv thiab siv. Nws ua lub luag haujlwm tseem ceeb hauv thaj chaw ntawm kev sib xyaw tshuaj, tshuaj tua kab hluavtaws, kev sib koom ua ke chemistry, thiab cov ntaub ntawv organic optoelectronic. Los ntawm synthesis thiab functionalization, cov tebchaw nrog cov qauv tshwj xeeb thiab cov khoom muaj peev xwm tuaj yeem tau txais los ua kom tau raws li qhov xav tau ntawm ntau qhov chaw thiab kev siv.

Molecular nta

2-Bromo-3-pyridinecarboxaldehyde muaj 6-tus neeg koom nrog pyridine nplhaib (ib lub nplhaib uas muaj nitrogen-muaj ntxhiab heterocycle) nrog ob qhov hloov pauv:

Bromine (Br): Ib pawg electron muaj zog- rho tawm pab pawg uas qhib lub nplhaib pyridine rau kev hloov pauv nucleophilic (xws li Suzuki, Heck, lossis Buchwald-Hartwig couplings).

Aldehyde (-CHO): Ib pawg neeg ua haujlwm muaj zog heev uas koom nrog cov tshuaj tiv thaiv condensation (xws li, imine tsim, reductive amination) thiab cov txheej txheem oxidation/txo.

Teb Chaws

Lub compound lub reactivity stems los ntawm interplay ntawm nws ob functional pab pawg:

Nucleophilic Aromatic Hloov (SNAr): Lub bromine atom tuaj yeem hloov tau los ntawm nucleophiles (piv txwv li, amines, thiols, lossis boronic acids) nyob rau hauv cov xwm txheej yooj yim, ua kom muaj kev sib txawv ntawm cov khoom sib txawv.

Condensation Reactions: Cov pab pawg aldehyde reacts nrog cov thawj amines los tsim imines, uas yuav txo tau mus rau theem nrab amines siv txo cov tshuaj xws li sodium borohydride (NaBH₄).

Oxidation/Reduction: Cov aldehyde tuaj yeem oxidized rau carboxylic acid (siv Jones reagent) lossis txo kom muaj cawv (siv NaBH₄).

Hla -Cov Kev Sib Txuas Sib Txuas: Cov bromine atom koom nrog palladium-catalyzed couplings (xws li Suzuki, Sonogashira) los ua cov pa roj carbon-carbon lossis carbon-heteroatom bonds.

Cov kev no ua rau 2-bromo-3-pyridinecarboxaldehyde ib lub linchpin nyob rau hauv ntau kauj ruam syntheses, qhov uas yuav tsum tau ua raws li functionalization.

Nws yog ib qho complex organic compound uas tuaj yeem ua ke los ntawm ntau txoj hauv kev.

1. Hantzsch pyridine synthesis method:

Cov tshuaj tiv thaiv formula yog raws li nram no:

C₅H₄BrN+2C₃H₂N₂+ CH₄N₂S → C₆H₄BrNO

Qhov no yog ib txoj kev siv feem ntau rau kev sib txuas 2-Bromo-3-pyridinecarboxaldehide, nrog rau cov kauj ruam tshwj xeeb raws li hauv qab no:

Kauj Ruam 1: Npaj cov reactants:

Sib tov 2-bromopyridine thiab malononitrile nyob rau hauv ib tug molar piv ntawm 1: 2, thiab ntxiv thiourea raws li ib tug catalyst. Tus nqi ntawm cov reactants tuaj yeem hloov kho raws li xav tau.

Kauj Ruam 2: Reaction nce qib:

Ntxiv cov reactants tau los ntawm kev sib xyaw hauv cov kauj ruam 1 mus rau cov tshuaj tiv thaiv cov tshuaj tiv thaiv thiab ua rau cov tshuaj tiv thaiv raws li qhov tsim nyog cov tshuaj tiv thaiv. Cov tshuaj tiv thaiv kub feem ntau yog nyob nruab nrab ntawm 150 thiab 200 degrees Celsius, thiab cov nitrogen qhuav ntws hauv cov kuab tshuaj -dawb tej yam kev mob yuav siv tau. Lub sij hawm tshuaj tiv thaiv nyob ntawm qhov kev sim tshwj xeeb, feem ntau yog nyob ntawm cov xuab moos mus rau hnub.

Nyob rau hauv cov tshuaj tiv thaiv no, thiourea ua raws li ib tug catalyst, txhawb kev loj hlob ntawm cov tshuaj tiv thaiv. Vim yog qhov kub thiab txias, qhov tsim ntawm C-C bonds tuaj yeem tshwm sim. Cov khoom kawg uas tsim tawm yog 2-Bromo-3-pyridinecarboxaldehide.

Kauj Ruam 3: Txias thiab crystallization:

Tom qab cov tshuaj tiv thaiv tiav, txias cov tshuaj tiv thaiv rau hauv chav tsev kub lossis kub kub thiab ua rau crystallization. Lub crystallization ntawm cov khoom tuaj yeem raug ntxias los ntawm maj mam ntxiv cov kuab tshuaj uas tsim nyog (xws li ethanol lossis ether solvents). Thaum lub sij hawm crystallization txheej txheem, cov khoom precipitate los ntawm cov tshuaj nyob rau hauv cov khoom.

Kauj Ruam 4: Purification thiab ziab:

Centrifuge los yog lim cov khoom crystallized cais cov khoom. Tom qab sib cais, cov khoom tuaj yeem ntxuav nrog cov kuab tshuaj tsim nyog kom tshem tawm cov impurities. Thaum kawg, cov khoom tau qhuav nyob rau hauv qhov tsim nyog kom tau txais siab -purity 2-Bromo-3-pyridine carboxaldehide.

2. Knoevenagel Condensation cov tshuaj tiv thaiv:

Cov tshuaj tiv thaiv formula yog raws li nram no:

C₅H₄BrN + C₄H₈O₃+C₆H₁₅N → C₆H₄BrNO

Hauv cov tshuaj tiv thaiv no, acyl thiab carboxyl pawg tsim C-C daim ntawv cog lus los ntawm cov tshuaj tiv thaiv Condensation. Cov khoom kawg uas tsim tawm yog 2-Bromo-3-pyridinecarboxaldehide.

Cov kauj ruam tshwj xeeb yog raws li nram no:

Kauj Ruam 1: Dissolve 2-bromopyridine thiab malonic acid (tus sawv cev carboxylic acid) hauv cov organic hnyav. Ethanol yog cov kuab tshuaj uas nquag siv.

Kauj Ruam 2: ntxiv ib qho alkaline catalyst, xws li triethylamine, los txhawb cov tshuaj tiv thaiv Condensation.

Kauj Ruam 3: Ua kom sov cov tshuaj thiab ua cov tshuaj tiv thaiv ntawm qhov kub thiab txias. Feem ntau siv cov tshuaj tiv thaiv kub yog 80-100 degrees Celsius.

Kauj Ruam 4: Tom qab cov tshuaj tiv thaiv ua tiav, txias cov tshuaj thiab ua rau kev kho acidification los tsim cov khoom lag luam 2-Bromo-3-pyridinecarboxaldehide.

Kauj ruam 5: Purify thiab crystallize cov khoom kom tau ib tug siab -purity compound.

Cov no tsuas yog ob txoj hauv kev xwb, thiab muaj ntau txoj hauv kev sib txuas rau 3-Pyridinecarboxaldehyde, 2-bromo-. Nws yuav tsum raug sau tseg tias txhua txoj kev sib xyaw ua ke muaj nws qhov tshwj xeeb zoo thiab siv tau, thiab yuav tsum tau hloov kho thiab kho kom zoo raws li qhov xwm txheej tshwj xeeb hauv kev ua haujlwm tiag tiag.

► Synthesis ntawm Kinase Inhibitor rau Kev Kho Mob Cancer

1) Keeb kwm

Kinase inhibitors yog ib chav kawm ntawm cov tshuaj tiv thaiv kab mob uas tiv thaiv kev ua haujlwm ntawm cov protein kinases, enzymes koom nrog hauv cell signaling thiab proliferation. Pyridine-raws li scaffolds muaj nyob rau hauv kinase inhibitor tsim vim lawv muaj peev xwm ua raws li ATP-binding sites. Cov kws tshawb fawb ntawm lub tuam txhab kws tshuaj nrhiav kev tsim kho tshiab inhibitor tsom mus rau epidermal growth factor receptor (EGFR), kinase overexpressed hauv ntau cov qog nqaij hlav.

2) Lub hom phiaj

Synthesize ib pyridine- muab tau los ntawm lub zog siab thiab kev xaiv rau EGFR siv 2-bromo-3-pyridinecarboxaldehyde ua ib qho tseem ceeb nruab nrab.

3) Kev sim ntsuas

Synthesis ntawm Core Structure:

2-Bromo-3-pyridinecarboxaldehyde tau hnov ​​​​mob nrog aniline hauv ethanol nyob rau hauv reflux los tsim ib qho imine intermediate ntawm condensation.

Lub imine tau txo qis siv sodium borohydride (NaBH₄) los ua 2-bromo-N-phenylpyridin-3-amine, lub tsev thaiv tseem ceeb rau kev ua haujlwm ntxiv.

Hla -Coupling Reaction:

Lub bromine atom ntawm 2- txoj hauj lwm underwent Suzuki-Miyaura coupling nrog ib tug boronic acid derivative (4-fluorophenylboronic acid) nyob rau hauv muaj palladium (II) acetate (Pd (OAc)₂) thiab ib tug ligand (triphenylphosphine).

Cov kauj ruam no tau qhia txog pawg fluorophenyl, txhim kho lipophilicity thiab khi affinity.

Kev hloov kho zaum kawg:

Cov pab pawg aldehyde tau oxidized rau carboxylic acid siv Jones reagent (chromic acid nyob rau hauv sulfuric acid), yielding lub hom phiaj compound: N-(4-fluorophenyl)-2-(4-fluorophenyl)pyridine-3-carboxamide.

4) Cov txiaj ntsig

Tawm tswv yim: 72% tshaj peb kauj ruam.

Kev ua si lom neeg:

Cov tshuaj tiv thaiv EGFR kinase kev ua haujlwm nrog IC₅₀ ntawm 12 nM hauv kev tshuaj xyuas enzymatic.

Kev tshawb fawb hauv vitro ntawm A431 cov qog nqaij hlav qog noj ntshav (overexpressing EGFR) tau pom GI₅₀ (kev loj hlob inhibition) ntawm 0.8 μM.

Selectivity: Lub compound tau nthuav tawm 50-fold selectivity dua lwm cov kinases (piv txwv li, VEGFR, CDK2), txo qis cov hom phiaj toxicity.

5) Kev cuam tshuam

Cov ntaub ntawv no qhia tau hais tias yuav ua li cas 2-bromo-3-pyridinecarboxaldehyde ua kom muaj kev sib dhos sai ntawm cov kinase inhibitors. Nws cov aldehyde thiab bromine pawg muab orthogonal reactivity rau sequential functionalization, ib lub tswv yim tam sim no dav saws nyob rau hauv tshuaj chemistry.

►Functionalization ntawm Graphene Oxide rau Enhanced Composite Materials

1) Keeb kwm

Graphene oxide (GO) yog cov khoom siv nrov tshaj plaws hauv cov khoom siv polymer vim nws lub zog txhua yam thiab hluav taws xob conductivity. Txawm li cas los xij, GO's hydrophilic xwm txwv nws qhov kev sib cais hauv cov tsis yog -polar polymers. Cov kws tshawb fawb tau nrhiav tshuaj kho GO siv 2-bromo-3-pyridinecarboxaldehyde los txhim kho kev sib raug zoo nrog epoxy resins.

2) Lub hom phiaj

Covalently graft 2-bromo-3-pyridinecarboxaldehyde mus rau GO thiab tshuaj xyuas cov khoom sib xyaw thermal thiab cov khoom siv tshuab.

3) Kev sim ntsuas

GO Hloov kho:

GO tau tawg mus rau hauv dimethylformamide (DMF) thiab sonicated rau 2 teev.

2-Bromo-3-pyridinecarboxaldehyde (5 eq.) thiab sodium hydroxide (NaOH, 10 eq.) tau ntxiv, pib cov tshuaj tiv thaiv nucleophilic hloov pauv ntawm GO's epoxide pawg thiab aldehyde's -carbon.

Composite Fabrication:

Kev hloov kho GO (GO-Py) tau sib xyaw nrog epoxy resin (diglycidyl ether ntawm bisphenol A, DGEBA) thiab cov tawv tawv (triethylene tetramine, TETA).

Cov sib tov tau kho ntawm 120℃rau 4 teev los tsim ib zaj duab xis sib xyaw.

Yam ntxwv:

Thermal stability tau soj ntsuam los ntawm kev ntsuas thermogravimetric (TGA).

Cov khoom siv tshuab tau ntsuas los ntawm kev ntsuas tensile.

4) Cov txiaj ntsig

Grafting Efficiency: Fourier-transform infrared spectroscopy (FTIR) paub tseeb tias muaj pyridine rings ntawm GO-Py.

Thermal stability:

Qhov pib degradation kub ntawm cov khoom sib xyaw tau nce los ntawm 35℃piv rau unmodified GO / epoxy.

Mechanical Properties:

Tensile zog txhim kho los ntawm 22%, los ntawm 45 MPa (tsis hloov kho) mus rau 55 MPa (GO-Py).

Elongation ntawm kev tawg tau nce 15%, qhia tias muaj kev ntxhov siab zoo dua.

5) Kev cuam tshuam

Cov ntaub ntawv no qhia txog yuav ua li cas 2-bromo-3-pyridinecarboxaldehyde tuaj yeem txuas cov inorganic nanomaterials thiab organic polymers. Lub nplhaib pyridine aromaticity txhim kho qhov sib txuas ntawm lub ntsej muag, ib txoj hauv kev siv tau rau lwm cov ntaub ntawv 2D xws li molybdenum disulfide (MoS₂).

► Bioconjugation rau Protein Labeling

1) Keeb kwm

Site-Kev sau npe tshwj xeeb protein yog qhov tseem ceeb rau kev kawm txog kev ua haujlwm ntawm cov protein, txhim kho kev kuaj mob, thiab tsim kho biotherapeutics. Cov pab pawg aldehyde nyob rau hauv 2-bromo-3-pyridinecarboxaldehyde tuaj yeem hnov ​​​​mob nrog lysine residues hauv cov proteins los ntawm kev txo qis, ua kom ruaj khov covalent bonds.

2) Lub hom phiaj

Sau npe rau N-terminus ntawm ntsuab fluorescent protein (GFP) siv 2-bromo-3-pyridinecarboxaldehyde thiab tshuaj xyuas cov ntawv sau ua haujlwm.

3) Kev sim ntsuas

Conjugation Reaction:

Recombinant GFP (1 mg / mL) yog incubated nrog 2-bromo-3-pyridinecarboxaldehyde (10 eq.) nyob rau hauv phosphate buffer (pH 7.4) rau 2 teev ntawm chav tsev kub.

Sodium cyanoborohydride (NaBH₃CN, 5 eq.) tau ntxiv los txo cov imine nruab nrab mus rau amine ruaj khov.

Purification:

Lub conjugate tau huv si siv qhov loj -exclusion chromatography (SEC).

Yam ntxwv:

Labeling efficiency tau txheeb xyuas los ntawm UV-Vis ​​spectroscopy (absorbance ntawm 280 nm rau cov protein, 340 nm rau pyridine).

Fluorescence siv tau ntsuas los ntsuas GFP kev ua haujlwm tom qab-labeling.

4) Cov txiaj ntsig

Labeling Efficiency: 85% ntawm GFP molecules tau conjugated, raws li kev txiav txim los ntawm pyridine absorbance.

Fluorescence Retention: Lub conjugate khaws 92% ntawm haiv neeg GFP cov fluorescence, qhia tias muaj kev cuam tshuam tsawg kawg nkaus.

Pawg Spectrometry: ESI-MS tau lees paub qhov nce ntawm 185 Da (ib yam nrog ib qho pyridinecarboxaldehyde moiety ib GFP).

5) Kev cuam tshuam

Txoj kev tshawb no qhia txog kev siv hluav taws xob ntawm 2-bromo-3-pyridinecarboxaldehyde hauv bioconjugation. Nws qhov me me thiab qhov ua kom muaj zog ua rau nws zoo dua rau cov fluorescent dyes loj dua, uas feem ntau cuam tshuam nrog cov protein ua haujlwm. Cov tswv yim zoo sib xws tam sim no tau siv los sau cov tshuaj tiv thaiv rau immunohistochemistry.

2-Bromo-3-pyridinecarboxaldehyde yog brominated aldehyde compound uas muaj ib lub nplhaib pyridine, nrog cov mis molecular C ₆ H ₄ BrNO thiab ib qho hnyav molecular ntawm 186. Qhov 2-txoj hauj lwm ntawm lub nplhaib pyridine nyob rau hauv nws cov qauv yog hloov los ntawm ib tug bromine atom muab ib tug tshwj xeeb atom, thiab ib tug tshwj xeeb atoms. tshuaj khoom. Raws li cov organic synthesis nruab nrab, nws yog dav siv hauv kev tshawb fawb tshuaj thiab kev loj hlob, tshuaj tua kab synthesis, thiab cov ntaub ntawv tshawb fawb. Piv txwv li, nyob rau hauv cov tshuaj synthesis, pawg aldehyde tuaj yeem koom rau hauv cov tshuaj tiv thaiv condensation los tsim cov pob txha heterocyclic, thaum lub bromine atom tuaj yeem qhia cov pab pawg ua haujlwm los ntawm kev hloov cov tshuaj tiv thaiv, muab kev yooj yim rau cov tshuaj molecule tsim.

 

Kev sib cuag ntawm daim tawv nqaij: Kev sib cuag ncaj qha tuaj yeem ua rau daim tawv nqaij liab, khaus, hlwv, thiab thaum mob hnyav, hu rau dermatitis.
Mechanism: Aldehyde pawg covalently khi nrog cov amino pawg hauv daim tawv nqaij proteins los ua Schiff hauv paus, cuam tshuam cov tawv nqaij barrier muaj nuj nqi; Lub xub ntiag ntawm bromine atoms tuaj yeem txhim kho nws lipophilicity thiab txhawb kev nkag mus rau hauv cov txheej txheem epidermal.
Kev sib cuag ntawm qhov muag: mob qhov muag mob hnyav, tshwm sim raws li conjunctival congestion, tearing, photophobia, thiab txawm tias lub pob ntseg ntawm epithelial puas.
Mechanism: Cov pab pawg Aldehyde hnov ​​​​mob nrog cov pob txha pob txha los ua cov protein denaturation, thaum bromine atoms tuaj yeem ua rau oxidative kev ntxhov siab thiab ua rau cov pob txha puas.

 

Kev ua pa ua pa: Kev nqus pa los yog hmoov av tuaj yeem ua rau khaus nasopharynx, hnoos, thiab ua pa nyuaj. Kev kis mus ntev yuav ua rau mob hawb pob lossis mob ntsws ntsws ntev (COPD). Aldehyde pawg khi rau cov proteins hauv cov pa mucosal epithelial hlwb, cuam tshuam mucosal kev ncaj ncees; Bromine atoms tuaj yeem ua rau muaj kev mob tshwm sim los ntawm kev tsim cov pa oxygen reactive (ROS).

 

Cov kab mob hauv plab zom mov: xeev siab, ntuav, mob plab, raws plab, thiab thaum mob hnyav, plab hnyuv los ntshav lossis daim siab puas tsuaj tuaj yeem tshwm sim. Cov nyhuv corrosive ncaj qha ntawm aldehyde pawg ntawm plab hnyuv mucosa, nrog rau kev txhawb nqa ntawm lub plab zom mov los ntawm hydrogen bromide tsim los ntawm cov metabolism ntawm bromine atoms hauv lub cev; Lub siab, uas yog lub hauv paus tseem ceeb ntawm cov kab mob metabolic, yuav muaj kev nce qib transaminase vim oxidative kev nyuaj siab.
Mob lom lom: kiv taub hau, qaug zog, tsis meej pem, thiab nyob rau hauv mob hnyav, coma, convulsions, thiab txawm ua pa thiab circulatory tsis ua hauj lwm. Aldehyde pawg cuam tshuam nrog cov paj hlwb los ntawm kev khi rau neurotransmitter receptors; Bromine atoms tuaj yeem cuam tshuam mitochondrial respiratory saw, ua rau cellular zog metabolism teeb meem.

Cim npe nrov: 2-bromo-3-pyridinecarboxaldehyde cas 128071-75-0, lwm tus neeg, manufacturers, hoobkas, lag luam wholesale, yuav, nqe, tej, kev muag khoom