6-Chloropurine CAS 87-42-3

Shaanxi BLOOM Tech Co., Ltd. yog ib qho ntawm cov tuam ntxhab thiab cov muag khoom ntawm 6-chloropurine cas 87-42-3 hauv Suav teb. Txais tos rau cov lag luam wholesale bulk zoo 6-chloropurine cas 87-42-3 muag ntawm no los ntawm peb lub hoobkas. Kev pabcuam zoo thiab tus nqi tsim nyog muaj.

6-Chloropurineyog ib qho tseem ceeb purine derivative thiab organic synthetic intermediate. Nws cov qauv yog ua raws li cov purine nucleus, nrog rau ib qho hydrogen atom hloov los ntawm chlorine atom. Cov yam ntxwv tseem ceeb tshaj plaws ntawm cov tshuaj no yog nyob rau hauv cov tshuaj muaj zog ntawm cov tshuaj chlorine atom ntawm C6 txoj hauj lwm hauv nws cov molecule, uas ua rau nws yooj yim hloov los ntawm ntau yam nucleophilic reagents (xws li amines, cawv, los yog thioalcohols), ua kom muaj txiaj ntsig thiab qhia kev sib xyaw ua ke ntawm cov tshuaj molecules 3}, purines thiab purines. bioactive compounds. Raws li qhov tseem ceeb reactivity, nws plays lub luag hauj lwm tseem ceeb thiab irreplaceable nyob rau hauv lub teb ntawm tshuaj chemistry thiab organic synthesis. Nws yog ib qho tseem ceeb pib cov khoom siv thiab cov hauv paus hauv paus rau kev sib txuas ntau yam tshuaj tiv thaiv -cov tshuaj tiv thaiv kab mob (xws li thiopurine), tshuaj tiv thaiv kab mob, thiab tshuaj tiv thaiv kab mob. Tsis tas li ntawd, raws li halogenated analogue ntawm adenine, nws kuj yog siv los ua kev sojntsuam lossis inhibitor hauv kev tshawb fawb biochemical los cuam tshuam thiab tshawb nrhiav cov purine metabolic txoj hauv kev thiab cov txheej txheem biosynthesis ntawm nucleic acids, ua kom pom nws tus nqi dual ntawm kev sib txuas cov kev tshawb fawb thiab kev kho mob.

6-Chloropurineyog cov neeg sawv cev zoo tshaj plaws thiab cov khoom siv roj ntsha hauv cov purine heterocyclic compounds, nrog rau cov ntawv thov tseem ceeb tsom mus rau kev sib txuas ntawm cov tshuaj intermediates, kev tshawb fawb thiab kev loj hlob ntawm cov tshuaj tiv thaiv -cov qog / tshuaj tua kab mob, biochemical thiab molecular biology tshawb fawb, thiab organic synthetic chemistry. Lub siab reactivity ntawm nws 6-txoj hauj lwm chlorine atom ua rau nws yog ib tug tseem ceeb precursor rau tsim ntau yam purine derivatives, uas yuav hloov mus rau hauv core molecules xws li adenine, 6-mercaptopurine, nucleoside analogues, thiab lwm yam los ntawm nucleophilic hloov, coupling tshua, thiab lwm yam; Nyob rau tib lub sijhawm, nws tus kheej thiab cov khoom lag luam metabolic muaj cov haujlwm lom neeg uas cuam tshuam cov metabolism hauv purine thiab cuam tshuam nrog nucleic acid synthesis, qhia txog qhov tseem ceeb hauv kev kho cov kab mob xws li qog thiab kab mob kis.

Synthesis ntawm adenine thiab vitamin B4 (adenine phosphate)

 

Adenosine (6-aminopurine) yog cov ntsiab lus tseem ceeb ntawm nucleic acids thiab coenzymes (xws li ATP, NAD ⁺), nrog rau cov qauv niam txiv ntawm vitamin B4 (adenine phosphate). 6- chloropurine yog qhov tseem ceeb tshaj plaws kev lag luam nruab nrab rau kev sib txuas ntawm adenine.
Synthesis txoj kev: Nws tau txais 6-txoj hauj lwm nucleophilic hloov cov tshuaj tiv thaiv nrog ammoniating reagents xws li ammonia thiab methylamine nyob rau hauv cov cua kub thiab siab, qhov twg cov chlorine atom hloov los ntawm ib pawg amino, ncaj qha generating adenine; Adenosine yog phosphorylated kom tau txais cov vitamin B4 (adenine phosphate), uas muaj cov txiaj ntsig siab thiab kev tswj kom huv yooj yim, thiab yog txoj hauv kev tseem ceeb rau kev tsim cov vitamin B4 thoob ntiaj teb.

Daim ntawv thov tus nqi: Vitamin B4 yog siv los tiv thaiv thiab kho leukopenia thiab mob granulocytopenia, tshwj xeeb tshaj yog rau leukopenia tshwm sim los ntawm cov qog chemotherapy thiab radiotherapy; Adenosine yog cov khoom siv tseem ceeb rau kev sib xyaw ntau yam tshuaj nucleoside thiab kev npaj coenzyme. Qhov loj - nplai ntau lawm ntawm cov tshuaj no ncaj qha txhawb kev ruaj ntseg ntawm cov saw hlau ntawm cov vitamin B4 thiab cov khoom siv tshuaj.

Synthesis ntawm 6-mercaptopurine (6-mep) thiab thiopurine antitumor tshuaj

 

6-mercaptopurine (6-MP) yog ib qho classic purine raws li tshuaj tiv thaiv kab mob metabolic thiab tshuaj tiv thaiv qog siv rau kev kho mob ntawm lymphocytic leukemia, mob myeloid leukemia, thiab lwm yam mob. Cov tshuaj no yog ib qho tseem ceeb precursor rau synthesis ntawm 6-MP.
Synthesis mechanism: Nws reacts nrog thio reagents xws li sodium hydrosulfide thiab thiourea, thiab chlorine atom ntawm txoj hauj lwm 6 yog hloov los ntawm ib pawg thiol (SH) los tsim 6-mercaptopurine; Cov kev mob tshwm sim yog me me thiab xaiv tau zoo, ua rau nws yog cov kauj ruam tseem ceeb hauv kev tsim khoom ntawm 6-MP.

Daim ntawv thov txuas ntxiv: 6-MP tuaj yeem hloov kho ntxiv los ua ke cov khoom siv xws li azathioprine thiab mercaptopurine methylates. Ntawm lawv, azathioprine yog ib qho kev siv tshuaj tiv thaiv kab mob hauv kev kho mob, siv los kho cov kab mob autoimmune xws li mob caj dab rheumatoid thiab kab mob lupus erythematosus. Nws kuj tseem txhawb nqa tag nrho kev lag luam saw kev tshawb fawb thiab tsim cov tshuaj thiopurine los ntawm 6-MP.

Synthetic nucleoside antiviral/anti-cov tshuaj qog noj ntshav

 

Nucleoside analogues yog ib pawg tseem ceeb ntawm cov tshuaj tiv thaiv kab mob thiab tshuaj tiv thaiv -cov tshuaj qog nqaij hlav, nrog cov txheej txheem tseem ceeb yog "base ribose/deoxyribose" unit. Raws li lub hauv paus ntawm purine hauv paus, nws tuaj yeem ua ke nrog ribose, deoxyribose, thiab lawv cov derivatives los ua ke ntau yam tshuaj nucleoside intermediates.
Adefovir dipivoxil ntsig txog nruab nrab: Adefovir dipivoxil yog tshuaj tiv thaiv kab mob siab B uas tsim los ntawm Gilead Science. Nws thaiv cov kab mob rov ua dua los ntawm inhibiting kab mob siab B kab mob DNA polymerase. Nws cov qauv molecular muaj adenine puag, uas yog cov khoom siv tseem ceeb rau kev sib txuas ntawm cov tshuaj adenine chav tsev. Cov tshuaj core skeleton yog tsim los ntawm ammoniation, alkylation thiab lwm yam.

Lwm cov nucleoside analogues: Nws dhau 9- txoj hauj lwm N-alkylation cov tshuaj tiv thaiv nrog glycosides/glycosides xws li ribose thiab cyclopentyl pawg los ua ke 9-alkyl-6-chloropurine, uas yog tom qab ntawd hloov thiab hloov kho kom tau txais intermediates ntawm cov tshuaj tiv thaiv kab mob qog noj ntshav xws li kab mob qog noj ntshav; Lub caij no, cov pa roj carbon cyclic nucleoside analogues xws li 9-norbornene-6-chloropurine muab los ntawm 6-chloropurine nthuav tawm cov haujlwm tseem ceeb tiv thaiv RNA cov kab mob xws li Coxsackievirus thiab rhinovirus, ua rau lawv cov khoom siv lead ua tseem ceeb rau kev txhim kho tshuaj tiv thaiv kab mob.

Kev tiv thaiv tus kheej - qog kev ua haujlwm thiab cov txheej txheem ntawm kev ua

 

Cov tshuaj nws tus kheej muaj nruab nrab los tiv thaiv- qog ua haujlwm thiab tau pom tias muaj kev cuam tshuam inhibitory ntawm cell proliferation thiab induction ntawm apoptosis nyob rau hauv ntau hom qog. Nws cov txheej txheem ntawm kev ua haujlwm yog cuam tshuam nrog kev hloov pauv hauv cov metabolism thiab cuam tshuam purine metabolism.
Metabolic activation mechanism: Nws tuaj yeem metabolized los ntawm ob txoj hauv kev hauv lub cev: ① Glutathione S-transferase (GST) catalyzes thiab khi nrog glutathione (GSH) los tsim S-purine glutathione, uas yog ntxiv metabolized rau hauv 6-mercaptopurine (6-mercaptopurine).

6-mep yog qhib los ntawm xanthine guanine phosphoribosyltransferase (HGPRT) los tsim thioinosine acid (TIMP), uas yog thaum kawg hloov mus rau hauv thioguanine nucleotides (TGNs).TGNs yog incorporated rau hauv DNA / RNA, ua rau cov saw breakage, inhibition ntawm numorsis ntawm nucleotides (TGNs). ② Oxidized los ntawm xanthine oxidase (XO) mus rau 6-chlorouric acid, 6-chlorouric acid tuaj yeem cuam tshuam cov uricase thiab cuam tshuam nrog purine metabolism txoj hauv kev.

Synergistic anti-cov nyhuv qog: Thaum siv ua ke nrog Azaserine, purine synthesis inhibitor, nws nthuav tawm cov txiaj ntsig tseem ceeb hauv kev tiv thaiv qog nqaij hlav hauv nas leukemia thiab lymphoma qauv. Azaserine inhibits de novo purine synthesis, thiab 6-chloropurine metabolites cuam tshuam nrog nucleic acid replication, txhim kho kev tua cov qog hlwb.

Cov ntaub ntawv tshawb fawb preclinical: Kev sim hauv vitro tau pom tias cov tshuaj no muaj IC50 tus nqi kwv yees li 10-50 μ M rau tib neeg leukemia CCRF-CEM hlwb thiab HL-60 hlwb, thiab IC50 tus nqi kwv yees li 32 μ M rau mob qog noj ntshav HepG2 hlwb. Nws muaj toxicity tsawg rau lub cev ib txwm muaj thiab muaj qee yam qog selectivity.

Antiviral kev ua ntawm derivatives

 

Nws 9-alkylated thiab arylated derivatives muaj broad-spectrum tshuaj tiv thaiv kab mob, tshwj xeeb tshaj yog tiv thaiv kab mob RNA.
Antienterovirus kev ua ub no: 9-de-6-chloropurine (NCP) yog ib tug neeg sawv cev, uas muaj zog inhibitory nyhuv ntawm me me RNA kab mob xws li Coxsackievirus B pab pawg neeg thiab rhinovirus. Nws cov txheej txheem yuav yog los thaiv cov kab mob RNA replication thiab cuam tshuam nrog cov kab mob capsid sib dhos;

In vitro experiments have shown that NCP has an EC50 of approximately 0.5 μ M for Coxsackievirus B3 and low cytotoxicity (CC50>100 μ M), qhia nws lub peev xwm ua tshuaj tiv thaiv kab mob.
Antiherpesvirus kev ua si: Cov tshuaj no yog ua ke nrog acyclic guanosine analogue los ua ke cov purine acyclic nucleoside derivatives, uas muaj kev tiv thaiv kev tiv thaiv kab mob herpes simplex (HSV) thiab varicella zoster virus (VZV), thiab tuaj yeem siv los ua tus neeg sib tw ntxiv rau cov tshuaj tua kab mob nucleoside.

Cov ntaub ntawv pov thawj:

1. Sigma Aldrich . 6-Chloropurine Product Manual [EB/OL]. (2026-01-14) [2026-03-19] https://www.sigmaaldrich.com/US/en/product/aldrich/511617
2. MolAid. Lub cev thiab tshuaj lom neeg thiab kev siv ntawm 6-Chloropurine (CAS: 87-42-3) [EB/OL]. (2025-09-25) [2026-03-19] https://www.molaid.com/MS_145180
3. BenchChem Technical Support Team. Kev Sib Piv Cytotoxicity Analysis: 6-Chloropurine vs. nws Thio-analog 6-Mercaptopurine[R]. BenchChem, 2025. https://pdf.benchchem.com/169/A_Comparative_Cytotoxicity_Analysis_6_Chloropurine_vs_its_Thio_analog_6_Mercaptopurine.pdf
4. Elion, GB, et al. Ntawm cov teebmeem metabolic ntawm 6-Chloropurine [J]. Cancer Research, 1961, 21(8): 1047–1056. https://aacrjournals.org/cancerres/article -pdf/21/8/1047/2376753/crs0210081047.pdf
5. Hwang, YI, et al. Kev kuaj pom thiab cov txheej txheem ntawm kev tsim ntawm S-(6-purinyl) glutathione thiab 6-mercaptopurine hauv nas muab 6-chloropurine [J]. Phau ntawv Journal of Pharmacology and Experimental Therapeutics, 1993, 264(1): 41–46.
6. Novakova, L., et al . 9-Norbornyl-6-chloropurine Yog Novel Antileukemic Compound Interacting with Cellular GSH[J]. Anticancer Research, 2013, 33(8): 3163-3170. https://ar.iiarjournals.org/content/33/8/3163

Muaj ntau txoj hauv kev los ua ke6-Chloropurine, cov hauv qab no yog cov kev siv feem ntau:

Txoj Kev 1: Hoffmann cov tshuaj tiv thaiv:

Qhov no yog txoj kev ib txwm npaj rau nws. Nyob rau hauv txoj kev no, 2-amino-6-chloropurine yog rhuab mus rau 85℃nyob rau hauv NaOH tov, ua raws li los ntawm mesophase tsim, thiab ces hydrolyzed nyob rau hauv ib tug polar hnyav rau 30 min. Cov khoom ntawm hydrolysis yog nws.

Txoj Kev 2: Cov tshuaj Fluoride hloov pauv:

Qhov no yog ib txoj kev uas tsis ntev los no nrhiav tau hluavtaws uas tuaj yeem siv los tsim. Nyob rau hauv txoj kev no, 2-aminopurine yog reacted los tsim N4-ethyl-2-aminopurine. Cov tshuaj tiv thaiv ntawm cov tshuaj no nrog txhuas chloride triflate thiab ferric chloride raws li catalysts muab rau nws.

Txoj Kev 3: Catalytic chlorination ntawm cawv:

Txoj kev no yog ib txoj kev yooj yim heev thiab tuaj yeem siv los npaj cov khoom. Hauv txoj kev no, 2-aminopurine yog reacted nrog benzyl cawv hauv tetrahydrofuran. Qhov no yields N4-benzyl cawv los yog N4-tert-butanol-2-aminopurine. Cov tshuaj no tau hnov ​​​​qab ntxiv, ntxiv cov ferrous chloride thiab silver chloride ua catalysts. Cov tshuaj tiv thaiv no tsim cov khoom siv chlorinated raws li cov khoom lag luam.

Txoj Kev Plaub: Pyridine Catalyzed Chlorination:

Nov yog lwm txoj hauv kev los ua ke6-Chloropurine. Hauv txoj kev no, 2-aminopurine thiab potassium ferrocyanate tau tshwm sim hauv cov tshuaj pyridine. Qhov sib xyaw no yuav tsim nws los ntawm kev ntxiv sodium hydroxide thiab hydrogen chloride gas.

Hauv cov ntsiab lus, nws yog ib qho tseem ceeb ntawm cov organic compound, thiab muaj ntau txoj hauv kev los xaiv los ntawm. Txawm hais tias Hoffmann cov tshuaj tiv thaiv ib txwm siv yog txoj kev siv ntau tshaj plaws rau kev npaj cov khoom, lwm txoj kev yooj yim dua thiab muaj txiaj ntsig tau pom nyob rau xyoo tas los no. Cov txheej txheem kev npaj sib txawv yuav tsim cov txiaj ntsig sib txawv thiab cov khoom pov tseg hauv cov xwm txheej sib txawv, yog li nws yog qhov tseem ceeb tshwj xeeb los xaiv cov txheej txheem tsim nyog raws li qhov tshwj xeeb daim ntawv thov scenario.

stability:

Nws yog qhov ruaj khov ntawm chav tsev kub, tab sis nws yog qhov yooj yim rau decomposition los yog oxidation cov tshuaj tiv thaiv nyob rau hauv tej yam kev mob xws li lub teeb los yog kub. Nyob rau hauv qhov kev txiav txim ntawm cov oxidizing muaj zog, nws tuaj yeem oxidized rau 6-chlorouracil. Tsis tas li ntawd, cov khoom decomposition ntawm nws tuaj yeem tso cov pa phem, yog li nws yuav tsum tau ua tib zoo saib xyuas kev nyab xeeb.

Restorability:

Nws tuaj yeem cuam tshuam nrog cov tshuaj txo qis thiab tuaj yeem txo mus rau 6-chloro-9H-purine raws li qhov tsim nyog. Kev txo cov tshuaj tiv thaiv yuav tsum tau ua nyob rau hauv ib qho chaw inert thiab nyob rau ntawm qhov kub thiab txias.

Electrophilicity:

nws tuaj yeem hloov kho los ntawm kev hloov pauv cov tshuaj tiv thaiv thiab cov tshuaj tsw qab NMR hloov pauv. Piv txwv li, nws tuaj yeem cuam tshuam nrog amines los qhia cov neeg hloov tshiab ntawm 6-txoj hauj lwm. Tsis tas li ntawd, sodium trifluoromethanesulfonate tuaj yeem qhia aryl pawg xws li phenyl ntawm 6-txoj hauj lwm.

Acidity thiab alkalinity:

6-Chloropurinemuaj cov kua qaub nruab nrab-cov khoom siv hauv paus thiab tuaj yeem lees txais lossis tso cov protons raws li kev ua ntawm cov kua qaub muaj zog lossis cov hauv paus. Hauv dej, nws muaj pKa ntawm 7.02. Nyob rau hauv lub xub ntiag ntawm lub hauv paus tsis muaj zog, nws muaj peev xwm tsim ketal tebchaw, thiab cov tshuaj tiv thaiv yuav tsum tau nqa tawm nyob rau hauv alkaline tej yam kev mob.

Stability: Kev txiav txim siab zoo los ntawm kev cia khoom mus rau cov tshuaj tiv thaiv

Lub cev ruaj khov

Melting point thiab boiling point: Lub melting point yog siab tshaj 300℃(decomposition), thiab lub boiling point yog 449.6 ± 25.0 degree, qhia tau hais tias nws yog nyob rau hauv ib tug khoom lub xeev ntawm chav tsev kub thiab muaj thermal stability;

Solubility: Soluble nyob rau hauv dej, ether thiab dimethylformamide (DMF), nrog ib tug solubility ntawm 30 mg / mL nyob rau hauv DMSO ntawm 25 degree, thiab yuav tsum tau them nyiaj mloog mus rau qhov cuam tshuam ntawm kev xaiv hnyav ntawm cov tshuaj tiv thaiv efficiency.

Tshuaj stability

Phototoxicity: Cov tshuaj no nkag siab rau lub teeb, thiab qhov ntev - raug rau lub teeb yuav ua rau degradation, thiab nws yuav tsum tau muab cia rau hauv qhov chaw tsaus (xws li siv lub raj mis xim av reagent);

Thaum tshav kub kub decomposition txaus ntshai: Tej zaum yuav decompose thiab tsim cov pa roj carbon monoxide (xws li carbon monoxide, carbon dioxide, nitrogen oxides) ntawm qhov kub thiab txias, thiab yuav tsum tau ceev kom deb ntawm qhov hluav taws kub thiab siab - ib puag ncig kub;

Cov tshuaj tiv thaiv oxidation: Tej zaum yuav raug oxidized los ntawm cov oxidants muaj zog (xws li poov tshuaj permanganate) nyob rau hauv muaj cov oxidants muaj zog, thiab yuav tsum tsis txhob sib xyaw cia.

Optimization ntawm kev cia khoom

Kev tswj qhov kub thiab txias: luv- lub sij hawm cia tuaj yeem muab tso rau hauv lub tub yees 4 degree, thiab ntev - lub sij hawm cia yuav tsum tau khov ntawm -20℃lossis qis dua kom qeeb degradation;

Kev ntim khoom: Siv cov iav ntim los yog polyethylene ntim, tsis txhob sib cuag nrog cov hlau ions (xws li hlau, tooj liab), thiab tiv thaiv catalytic degradation;

Lub sijhawm ruaj khov: Raws li kev pom zoo khaws cia, lub sijhawm siv tau yog feem ntau tshaj 4 xyoo, tab sis yuav tsum tau kuaj cov ntsiab lus purity thiab impurity tsis tu ncua.

Cov tshuaj tiv thaiv kev ua si thiab kev sib raug zoo

Acid-base stability: Tej zaum yuav raug lub nplhaib- qhib los yog hydrolysis cov tshuaj tiv thaiv nyob rau hauv acidic los yog alkaline tej yam kev mob, thiab pH tswj yuav tsum tau;

Hlau catalysis: Sib cuag nrog tej yam hlau (xws li palladium, npib tsib xee) yuav ua rau catalytic degradation, thiab ib tug inert catalyst yuav tsum tau xaiv; Kev ua yeeb yam lom neeg: Ua ib qho khoom nruab nrab, 6-chloropurine tuaj yeem siv los npaj cov tshuaj tiv thaiv qog (xws li 6-mercaptopurine) thiab cov tshuaj tua kab mob. Nws reactivity ncaj qha cuam tshuam rau purity ntawm lub hom phiaj khoom.

Kev nyab xeeb thiab kev ruaj ntseg kev coj ua hauv kev lag luam siv

 

Pharmaceutical synthesis teb

Raws li lub precursor ntawm adenine thiab 6-mercaptopurine, nws stability ncaj qha cuam tshuam rau purity ntawm cov tshuaj. Thaum lub sij hawm tsim cov txheej txheem, kev soj ntsuam nruj ntawm qhov kub thiab txias, lub teeb raug, thiab cov av noo yuav tsum tsis txhob muaj kev cuam tshuam sab nraud;

Case: Lub tuam txhab kws tshuaj tau ntsib cov khoom lag luam degradation vim qhov kub thiab txias hloov pauv thaum lub sijhawm khaws cia, thiab thaum kawg daws tau qhov teeb meem los ntawm kev ua kom zoo tshaj qhov kev cia txias txias.

Kev tshawb fawb biochemical

Thaum siv nyob rau hauv lub synthesis ntawm 9-alkylpurine thiab 6-mercaptopurine, lub purity ntawm reagents (Ntau tshaj los yog sib npaug rau 98%) yuav tsum tau ua kom tsis txhob cuam tshuam los ntawm impurities nyob rau hauv cov kev sim tau tshwm sim;

Cov lus qhia txog kev nyab xeeb: Cov chaw soj nstuam yuav tsum tau nruab nrog cov khoom siv biosafety, thiab cov neeg ua haujlwm yuav tsum tau txais kev cob qhia ua haujlwm kom txo tau qhov kev pheej hmoo ntawm kev raug mob ntev -.

Industrial ntau lawm optimization

Los ntawm kev siv inert gas tiv thaiv thiab automated tswj systems, qhov kev pheej hmoo ntawm tib neeg lub lag luam tuaj yeem txo qis, thaum txhim kho cov khoom ruaj khov;

Txoj Kev: Kev nce qib ntawm cov txheej txheem tshuaj ntsuab (xws li cov kuab tshuaj -dawb synthesis) yuav tsum txo qis kev nyab xeeb thiab ib puag ncig.

Cim npe nrov: 6-chloropurine CAS 87-42-3, lwm tus neeg, manufacturers, hoobkas, lag luam wholesale, yuav, nqe, tej, kev muag khoom