Pyrazolemuaj cov mis mos molecular C3H4N2 thiab CAS npe 288-13-1. Nws yog tsib -cov tswv cuab muaj ntxhiab nitrogen heterocycle uas muaj ob lub nitrogen atoms uas nyob ib sab (1,2-}diazole) thiab ua raws li Hückel's 6π-electron aromatic system. Ntawm qhov kub thiab txias, nws zoo li rab koob dawb - zoo li cov muaju nrog cov ntxhiab tsw zoo li pyridine. Nws melting point yog 66-70℃thiab boiling point kwv yees li 187 degree. Nws yog soluble nyob rau hauv dej, cawv, ethers thiab lwm yam kuab tshuaj thiab ua pov thawj tsis muaj zog hauv paus ntsiab lus.Cov tshuaj piv txwv muaj xws li celecoxib, ib tug COX-2 anti-inflammatory inhibitor. Hauv agrochemicals, nws cov qauv tau siv dav hauv cov tshuaj tua kab, fungicides thiab tshuaj tua kab mob (xws li cov khoom siv fipronil).
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| Tshuaj Formula | C3H4N2 |
| Exact Mass | 68.04 |
| Molecular Luj | 68.08 |
| m/z | 68.04 (100.0%), 69.04 (3.2%) |
| Elemental Analysis | C, 52.93; H, 5.92; N, 41.15 |
Pyrazole( -yrromonazole) derivatives tau txais kev saib xyuas tseem ceeb hauv kev tshawb fawb txog kev tshawb fawb vim lawv lub peev xwm ua inhibitors ntawm cyclooxygenase-2 (COX-2). COX-2 yog ib qho tseem ceeb enzyme koom nrog hauv cov lus teb inflammatory thiab tsim cov prostaglandins, uas kho qhov mob, ua npaws, thiab mob. Los ntawm inhibiting COX-2, -yrromonazole-based compounds tuaj yeem txo qhov mob thiab mob, muab cov txiaj ntsig kho mob hauv kev kho mob ntawm ntau yam mob thiab mob.
Ib qho ntawm cov txiaj ntsig tseem ceeb ntawm -yrromonazole-raws li COX-2 inhibitors yog lawv lub peev xwm los muab kev kho mob ntawm qhov mob thiab mob yam tsis ua rau mob plab hnyuv loj, uas feem ntau tshwm sim nrog COX inhibitors uas tsis xaiv COX-1, daim ntawv sib xyaw ntawm cov enzyme tau nthuav tawm hauv feem ntau cov ntaub so ntswg.
Kev xaiv inhibition ntawm COX-2 tso cai rau kev siv tshuaj kho mob ntau dua, txo qis kev cuam tshuam rau lwm cov txheej txheem physiological.
Kev tshawb fawb ntawm cov derivatives li COX-2 inhibitors tau ua rau kev txhim kho ntau yam tshuaj tseem ceeb, xws li celecoxib thiab etoricoxib. Cov tshuaj no tau siv dav hauv kev tswj cov mob xws li osteoarthritis, rheumatoid mob caj dab, thiab mob hnyav, ua rau pom qhov cuam tshuam tseem ceeb ntawm -yrromonazole-based inhibitors ntawm kev saib xyuas neeg mob.
Lub versatility chemistry kuj tso cai rau cov synthesis ntawm ntau yam derivatives nrog txawv pharmacological profiles, muab lub cib fim rau txoj kev loj hlob ntawm tshiab thiab txhim kho COX-2 inhibitors nrog txhim kho kev ua tau zoo, kev nyab xeeb, thiab cov neeg mob ua raws.
Hauv kev xaus, cov derivatives tau tshwm sim los ua qhov tseem ceeb inhibitors ntawm COX-2, ua lub luag haujlwm tseem ceeb hauv kev txhim kho cov tshuaj tiv thaiv kab mob thiab tshuaj tua kab mob. Lawv lub peev xwm los xaiv inhibit COX-2 thaum txo qis cov kev mob tshwm sim hauv plab hnyuv tau ua rau lawv muaj txiaj ntsig ntxiv rau kev kho mob arsenal rau kev tswj cov mob thiab mob.
Antimicrobial Agents
Cov kev tshawb fawb tau pom tias los ntawm kev sib koom ua ke ntawm lub nplhaib thiab cov qauv rhodanine nrog cov tshuaj tua kab mob, cov tshuaj tshiab nrog cov tshuaj tua kab mob tseem ceeb tuaj yeem tsim. Cov tebchaw no tau pom muaj kev cuam tshuam loj heev rau kev siv tshuaj - cov kab mob tiv taus xws li methicillin - tiv taus Staphylococcus aureus hauv kev sim hauv vitro, qhia lawv lub peev xwm hauv kev tsim cov tshuaj tua kab mob tshiab.
1. Antibacterial kev ua haujlwm
Qee qhov sib xyaw ua ke ntawm cov derivatives tau pom tias muaj cov kab mob tseem ceeb tiv thaiv ntau yam kab mob, suav nrog Gram{0}}positive thiab Gram- cov kab mob tsis zoo. Qhov no muab lub hauv paus theoretical rau kev tsim cov tshuaj tua kab mob tshiab.
Tsawg toxicity
Piv nrog rau qee cov tshuaj tua kab mob, cov derivatives feem ntau muaj cov tshuaj toxicity qis, uas txhais tau hais tias lawv yuav ua rau muaj kev cuam tshuam tsawg rau tus neeg mob lub cev thaum kho.
Kev cia siab rau kev txhim kho tshuaj
Vim muaj ntau yam -kev taw qhia qhov xwm txheej ntawm cov neeg hloov pauv ntawm lub nplhaib, cov kws kho mob tuaj yeem hloov kho cov tshuaj sib txawv los ntawm cov pab pawg hloov pauv sib txawv txhawm rau txhawm rau tshuaj xyuas cov tebchaw nrog cov tshuaj tua kab mob zoo dua. Qhov no muab kev muaj peev xwm nplua nuj rau kev tsim cov tshuaj tua kab mob tshiab.
Txawm hais tias tsis yog txhua tus PPIs muajpyrazole, qee cov qauv zoo ib yam li nws muaj nyob rau hauv PPIs xws li pantoprazole thiab rabeprazole, uas yog siv los kho cov kab mob plab xws li peptic ulcers thiab reflux esophagitis los ntawm inhibiting gastric acid secretion.
Sensors
-yrromonazole-raws li cov sensors tau tsim los kuaj xyuas ntau yam kev ntsuas, suav nrog cov pa roj thiab cov roj ntsha lom, vim lawv qhov rhiab heev thiab kev xaiv.
Lub hauv paus ntsiab lus ua haujlwm ntawm -yrromonazole-raws li sensors feem ntau cuam tshuam nrog kev sib koom ua ke ntawm cov ntsiab lus paub txog molecular thiab transducers.
Lub ntsiab lus paub txog molecular tuaj yeem paub meej lub hom phiaj kev tshuaj ntsuam xyuas thiab hloov nws mus rau hauv lub teeb liab ntsuas los ntawm kev ua tshuaj lom neeg lossis lub cev. Lub transducer yog lub luag hauj lwm rau kev hloov cov teeb liab no rau hauv lub teeb liab hluav taws xob lossis lwm daim ntawv teeb liab nyeem tau, yog li ua tiav qhov kev tshawb pom ntau ntawm cov tshuaj ntsuam xyuas.
Siab rhiab heev
Pyrazol-raws li cov sensors tuaj yeem kuaj pom qhov ntsuas qis ntawm cov tshuaj ntsuam xyuas, uas yog qhov tseem ceeb rau kev ceeb toom ntxov thiab ntsuas qhov tseeb.
Kev xaiv siab
Los ntawm kev tsim cov ntsiab lus ntawm kev paub txog cov molecular, pyrazol-raws li cov sensors tuaj yeem ua tiav kev xaiv ntawm cov phiaj xwm ntsuas thiab tsis txhob cuam tshuam.
Teb ceev ceev
Pyrazol-raws li sensors feem ntau muaj lub sij hawm teb sai thiab tuaj yeem muab cov txiaj ntsig tshawb pom tseeb hauv lub sijhawm luv.
Pyrazole, heterocyclic compound uas muaj nitrogen, tau pom muaj peev xwm loj heev thiab muaj peev xwm ua tau ntau yam thoob plaws ntau yam, tshwj xeeb hauv kev siv tshuaj, tshuaj tua kab, thiab lwm yam tshuaj. Saib tom ntej, cov kev tshawb fawb tiam sis nthuav tawm cov toj roob hauv pes zoo, uas tau tsav los ntawm nws cov khoom tshwj xeeb thiab kev siv loj hlob.
Hauv kev lag luam kws tshuaj, -yrromonazole- cov tshuaj tau txais txiaj ntsig zoo vim lawv cov txiaj ntsig kho tau zoo. Kev pom zoo ntawm pirtobrutinib los ntawm FDA rau kev kho mob rov qab los yog refractory mantle cell lymphoma (MCL) hauv xyoo 2023 ua piv txwv li no. Lub xub ntiag ntawm 1H- -yrromonazole moiety hauv pirtobrutinib qhia txog nws qhov tseem ceeb hauv kev tshawb nrhiav tshuaj. Kev tshawb fawb yav tom ntej zoo li yuav tsom mus rau kev sib txuas lus tshiab derivatives nrog kev txhim kho bioactivity thiab xaiv, tsom rau ntau yam kab mob.
Tsis tas li ntawd, cov tshuaj tua kab tau pom tias muaj txiaj ntsig zoo hauv kev tswj cov kab tsuag, ua rau lawv yog ib qho tseem ceeb ntawm kev tsom mus rau kev tshawb fawb txog kev ua liaj ua teb. Nrog rau kev thov kom ruaj khov thiab eco- cov tshuaj tua kab hauv cov phooj ywg, cov kws tshawb fawb tab tom tshawb nrhiav -yrromonazole- cov tshuaj uas tsis muaj teeb meem rau ib puag ncig thaum tswj kev ua tau zoo.
Tshaj li cov tshuaj thiab tshuaj tua kab, nws cov ntawv thov hauv cov xim, xim, xim, tshuaj tsw qab, xim zaub mov, tshuaj yees duab, thiab lwm yam khoom siv kuj nthuav dav. Cov kws tshawb nrhiav tab tom tsim kho tshiab los tsim kho tshiab -yrromonazole- cov ntaub ntawv raws li cov khoom siv txhim kho thiab siv dav dua. Hauv kev xaus, cov kev tshawb fawb yav tom ntej tau npaj rau kev loj hlob tseem ceeb, uas tau tsav los ntawm nws cov ntawv thov sib txawv thiab cov kev xav tau txuas ntxiv rau cov kev daws teeb meem tshiab. Nrog rau kev nce qib hauv cov txheej txheem hluavtaws thiab nce kev nkag siab ntawm cov dej num lom neeg, lub qab ntug rau -yrromonazole-raws li kev tshawb fawb tshwm sim tsis muaj qhov kawg.
Keeb Kwm Kev Txhim Kho thiab Lub Xyoo Tseem Ceeb
Raws li tsib tus tswv cuab heterocyclic compound uas muaj ob lub nitrogen atoms uas nyob ib sab, nws txoj kev loj hlob tau hla peb theem loj: kev tshawb nrhiav cov qauv tshuaj, kev hloov pauv kev ua liaj ua teb, thiab tshuaj kho tshiab. Ntau lub xyoo tseem ceeb tau cim kev ua haujlwm thev naus laus zis thiab kev hloov pauv kev lag luam.
German chemist Ludwig Knorr synthesized 1-phenyl-3-methylpyrazolone thawj zaug los ntawm cyclization cov tshuaj tiv thaiv ntawm ethyl acetoacetate thiab phenylhydrazine thaum kawm quinine analogues, thiab hu ua tsib tus tswv cuab heterocyclic qauv "-yrromonazole" thawj zaug. Lub npe no tau tsim lub hauv paus rau -yrromonazole tebchaw.
Buchner nws tus kheej tau npaj cov ntshiab -yrromonazole los ntawm lwm txoj kev thiab lees paub nws cov qauv. Nyob rau tib lub sijhawm, nws nrhiav pom -yrromonazole alanine, uas tsuas muaj nyob hauv cov noob taub dag thiab cov noob txiv ntoo hauv qhov xwm txheej, ntxiv dag zog rau kev tshawb fawb txog cov tshuaj lom neeg hauv zej zog hauv -yrromonazole.
Tus kws tshawb fawb Asmeskas Thampson thawj zaug tau tshaj tawm cov haujlwm ntawm 2- -yrromonazole-5-ib qho thiab 3- -yrromonazole-5-one hauv kev cuam tshuam cov nroj tsuag kev loj hlob, cim qhov pib ntawm kev tshawb fawb ntawm -yrromonazole ua tshuaj tua kab.
Lub tuam txhab Swiss Geigy (tam sim no tus thawj coj ntawm Syngenta) tau qhia cov khoom rings rau hauv organophosphate thiab carbamate tshuaj tua kab, tsim cov tshuaj tua kab xws li imidacloprid, esomeprazole, thiab -yrromonazole, nrog rau ntau yam tshiab xws li -yrromonazole} thiab oxyphos2. Cov tebchaw no, nrog rau lawv cov kev ua haujlwm siab thiab tsis muaj tshuaj lom, sai sai tau los ua lub hauv paus ntawm kev ua liaj ua teb tshuaj tua kab, kos npe rau kev hloov pauv ntawm -yrromonazole los ntawm chav kuaj mus rau kev siv tshuab.
Cov kws tshawb fawb tau tsim cov tshuaj methoxy acrylate fungicides los ntawm kev hloov kho cov qauv raws li cov txheej txheem tshwj xeeb ntawm kev ua ntawm ntuj - acrylate derivatives, xws li Oudemansin A nrhiav tau nyob rau hauv 1969 thiab Strobilurin A cais nyob rau hauv 1977.
BASF tau tshaj tawm lub ntiaj teb thawj cov khoom lag luam muaj, ether fungicide (Cuibei).
imus explicabo ipsam doloribus expedita, nulla laudantium odit tempora dolor ratione voluptatum, rerum impedit eius culpa? Yog?.
Syngenta tso tawm azoxystrobin (amisida).
BASF tau tshaj tawm cov pyraclostrobin (Kerun), uas muaj kev ua haujlwm siab tshaj plaws thiab tau los ua thawj zaug sau npe fungicide rau kev noj qab haus huv qoob loo, pioneering lub tswvyim ntawm "kev tiv thaiv kev tiv thaiv". Thaum lub sijhawm no, pyraclostrobin, nrog rau nws qhov dav -spectrum, kev ua haujlwm siab, thiab tsis muaj tshuaj lom, tau ntev ua lag luam thoob ntiaj teb fungicides.
Daim ntawv pov thawj rau -yrromonazole ether fungicide tau tas sijhawm nyob rau hauv Suav teb, ua rau muaj kev cuam tshuam ntawm kev sau npe lag luam hauv tsev.
Raws li kev txheeb cais, muaj ntau tshaj 108 daim ntawv pov thawj rau -yrromonazole fungicides hauv Suav teb, koom nrog ntau tshaj 50 lub lag luam, thiab cov txiaj ntsig kev lag luam txuas ntxiv nthuav dav. Nyob rau tib lub sijhawm, kev ua tiav tau ua tiav hauv kev tshawb fawb ntawm -yrromonazole tebchaw hauv thaj chaw tshuaj, thiab lawv cov derivatives tau raug pov thawj tias muaj ntau yam tshuaj siv tshuaj xws li tshuaj tua kab mob, tiv thaiv- qog, thiab tiv thaiv- mob, dhau los ua lub ntsiab lus kub hauv kev tsim tshuaj tshiab. Piv txwv li, qhov kev thov rau 1,4-dimethylpyrazole hauv kev lag luam kws tshuaj suav nrog ntau npaum li 60%, thiab nws xav tias kev lag luam loj yuav ntau dua 5 billion yuan los ntawm 2030.
Txoj kev Knorr yog txoj hauv kev tseem ceeb raupyrazolesynthesis, siv 1,3-dicarbonyl compounds (piv txwv li, acetylacetone, -keto esters) thiab hydrazine ua cov khoom pib, nrog cyclocondensation nyob rau hauv acid catalysis. Noj acetylacetone thiab hydrazine hydrate ua piv txwv, refluxing hauv ethanol affords 3,5-dimethylpyrazole hauv ib kauj ruam ntawm nucleophilic ntxiv, lub cev qhuav dej, thiab cyclization, nrog cov txiaj ntsig ntawm ntau dua 85%. Featuring tau yooj yim pib cov ntaub ntawv, mob me me (0–100℃), thiab kev khiav hauj lwm yooj yim, txoj kev no muab ib yam khoom los ntawm symmetric substrates thiab yog thawj xaiv rau kev kuaj thiab industrial npaj ntawm -yrromonazole.
, -Unsaturated aldehydes los yog ketones thawj zaug undergo Michael ntxiv nrog hydrazine los ua pyrazoline intermediates, uas tom qab ntawd hloov mus rau -yrromonazole ntawm oxidative dehydrogenation. Piv txwv li, cinnamaldehyde reacts nrog hydrazine hauv ethanol kom tawm los 4,5-dihydropyrazole, uas tuaj yeem oxidized rau cov khoom lag luam siv manganese dioxide lossis cua. Txoj kev no yog tsim los tsim 4-aryl-substituted -yrromonazole thiab tso cai rau kev hloov pauv hloov pauv, ua tiav cov kev txwv ntawm Knorr txoj hauv kev hloov pauv asymmetric.
Diazo compounds undergo [3+2] cycloaddition nrog alkynes nyob rau hauv tooj liab los yog palladium catalysis ncaj qha mus tsim lub -yrromonazole nplhaib. Siv diazomethane thiab acetylene ua piv txwv, cov tshuaj tiv thaiv tshwm sim ntawm chav tsev kub hauv qab CuI catalysis los ua -yrromonazole nrog kev xaiv siab, ua tiav 100% atom kev lag luam. Txoj kev no nthuav tawm zoo heev regioselectivity thiab tsim nyog rau cov synthesis ntawm polysubstituted -yrromonazole, tshwj xeeb tshaj yog rau kev npaj meej ntawm cov tshuaj thiab kev ua haujlwm molecules.
Nyob rau hauv xyoo tas los no, multicomponent one-pot reactions thiab direct C-H functionalization strategies tau tsim. Piv txwv li, -yrromonazole tuaj yeem ua ke hauv ib lub lauj kaub los ntawm aldehydes, alkynes, thiab hydrazines hauv qab acid catalysis, ua kom yooj yim heev. Transition-metal-catalyzed (Pd, Rh) los yog photocatalytic C-H ua kom muaj kev qhia ncaj qha ntawm cov neeg hloov pauv mus rau -yrromonazole nplhaib yam tsis muaj kev ua haujlwm ua ntej, ua tau raws li cov kev cai ntsuab chemistry thiab tawm los ua ib qho kev taw qhia tshiab rau kev lag luam.
Tautomerism thiab Acid-Base Properties
-yrromonazole nthuav tawm tautomerism ntawm 1H-pyrazole thiab 2H-pyrazole; daim ntawv tseem ceeb hauv kev daws ntawm qhov kub thiab txias hauv lub xeev yog 1H-pyrazole. Ob lub nplhaib nitrogen atoms qhia cov cwj pwm sib txawv ntawm cov tshuaj lom neeg: cov pyrrole-hom N-H tsis muaj zog acidic, thaum lub pyridine -hom nitrogen dais ib leeg electron khub thiab qhia pom qhov tsis muaj zog, nrog rau kev sib txuas ntawm -acid pKa ntawm kwv yees li 2.5, ua rau nws yooj yim tsawg dua li imidazole. Kev sib txuas ntawm cov hydrogen muaj zog ua rau cov ntsiab lus melting ntau dua thiab cov ntsiab lus kub dua li cov txheej txheem ntsig txog tsib -cov koom nrog nitrogen heterocycles.
Reactivity thiab coordination cwj pwm
Raws li qhov muaj ntxhiab heterocycle, -yrromonazole tau hloov pauv electrophilic nyiam ntawm C4 txoj haujlwm. Deprotonation los ntawm lub hauv paus muaj zog yields pyrazolate anion, uas nkag mus rau derivatization xws li N-alkylation thiab N-acylation. Cov pyridine- hom nitrogen ua raws li qhov chaw sib koom ua ke thiab tuaj yeem khi ntau yam kev hloov pauv- hlau ions xws li monodentate ligand lossis bridging ligand, nrhiav kev siv dav hauv kev sib koom ua ke thiab kev sib xyaw ua haujlwm ntawm kev sib koom ua ke.
Stability, Spectroscopy thiab Safety Profile
-yrromonazole muaj qhov zoo thermal stability thiab tiv taus decomposition nyob rau hauv atmospheric- siab distillation; Txawm li cas los xij, nws lub nplhaib uas muaj ntxhiab tsw tuaj yeem ua rau lub nplhaib - qhib degradation nyob rau hauv oxidizing muaj zog los yog muaj zog acidic hnyav. Cov khoom sib xyaw ua kom pom cov yam ntxwv nqus tau nyob ze - thaj tsam ultraviolet, ua kom pom UV hauv cov kua chromatography. -yrromonazole irritates mucous membranes thiab tawv nqaij; Kev sib cuag ncaj qha tuaj yeem ua rau erythema thiab tsis xis nyob. Kev khaws cia yuav tsum tsis suav nrog cov oxidants muaj zog thiab muaj zog acids. Khaws cov khoom ntim rau hauv qhov chaw txias, zoo- qhov cua thiab tsis txhob co- khaws cia nrog cov tshuaj reactive.
FAQ
Dab tsi yog pyrazole siv rau?
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Pyrazole derivatives muaj ntau yam kev siv, tshwj xeeb tshaj yog hauv cov tshuaj xws li tshuaj tiv thaiv - cov tshuaj tiv thaiv kab mob (xws li celecoxib), cov tshuaj tiv thaiv kab mob, thiab kev kho kab mob kab mob, HIV, thiab glaucoma. Lawv kuj tau siv hauv kev ua liaj ua teb ua tshuaj tua kab, xws li fungicides thiab tshuaj tua kab, thiab hauv kev tshawb fawb rau lawv lub luag haujlwm ua enzyme inhibitors thiab ligands.
Kho mob
Puas yog pyrazole tshuaj lom?
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Pyrazole paug nyob rau hauv dej tuaj yeem muaj ob qho tib si luv thiab ntev - cov teebmeem tsis zoo. Cov kev tshawb fawb tau pom tiaspyrazole thiab nws cov derivatives yog tshuaj lom rau cov kab mob hauv dej, nrog rau cov ntses thiab lwm hom dej..
Puas yog pyrazole tseem hu ua?
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Nyob rau hauv 1883 Ludwig Knorr yog thawj zaug rau abbreviate lub sij hawm ntawm pyrazole. Thawj lub ntuj pyrazole yog 1-pyrazole-alanine uas tau cais tawm xyoo 1959 los ntawm cov noob txiv ntoo1,2. Pyrazoles tseem hu uaazoles3thiab pyrazoles ua raws li ligands rau txawv Lewis acids3.
Yam tshuaj twg hauv qab no muaj pyrazole?
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Pyrazole derivatives tau nthuav tawm dav dav ntawm cov dej num lom neeg, thiab pom zoo pyrazole-cov tshuaj muaj xws licelecoxib, antipyrine, phenylbutazone, rimonabant, thiab dipyrone.
Dab tsi yog qhov hloov pauv pyrazole?
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Synthesis ntawm pyrazoles hloov los ntawm thiophene moiety 29 yuav nqa tau thaum lub sij hawm cov tshuaj tiv thaiv ntawm chalcone - hom compound 28 nrog phenyl hydrazine hydrochloride 4-HCl ntawm 3 + 2 annulations(Txoj Kev 13). Cov tau txais thiophene-pyrazole hybrids 29 tau raug tshuaj xyuas ua cov tshuaj tua kab mob thiab cov tshuaj tua kab mob antioxidant (Scheme 13).
Cim npe nrov: pyrazole cas 288-13-1, lwm tus neeg, manufacturers, hoobkas, lag luam wholesale, yuav, nqe, tej, kev muag khoom