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Inta badan Hopeocycles ee Dunida

Inta badan Hopeocycles ee Dunida

Xeryahooda Heterocyclic

Qalabka heterocyclic, oo sidoo kale loo yaqaano qaab dhisma wuxuu aasaas u yahay maaddada ku jirta aaladaha laba waxyaalood oo kala duwan sida xubno ka mid ah giraangiisa. Xeryaha Heterocyclic waxaa laga yaabaa inay noqdaan kuwa ugu kala duwan iyo tirada ugu badan ee qoyska qoyska.

Iyadoo aan loo eegin waxqabadka iyo qaabdhismeedka, walax kasta oo carbocyclic ah ayaa loo rogi karaa noocyo kala duwan oo heterosikid ah adigoo badalaya hal ama dhowr kaarbood oo kumbuyuutar leh weel kala duwan. Natiijo ahaan, heterocycles ayaa bixiya barmaamijka is-weydaarsiga cilmi-baarista ee goobo kala duwan oo ay ku jiraan laakiin aan ku koobneyn daawooyinka, daawooyinka, falanqaynta, iyo kiimikada organic ee xeryahooda heterocyclic.

Tusaalooyinka ugu muhiimsan ee xeryaha heterosikliyada waa badi daawooyinka, asiidhooyinka nucleiciga ah, intooda badan ee qalabka dabiiciga ah iyo dabiiciga ah, iyo badiba qaylo dhaansiga sida cellulose iyo alaabta la xidhiidha.

Qoondaynta

Inkasta oo xeryahooda heterocyclic ay noqon karaan xeryahooda ama kuwa asaliga ah, inta badan waxay leeyihiin ugu yaraan hal caro. Xeryahanadan waxaa loo kala saari karaa habka elektaroonigga ah. Xeryahooda heterocyclic-ta ah waxay u dhaqmaan si isku mid ah walxaha deriska ah. Natiijada, tetrahydrofuran iyo piperidiin waa anshaxyo caadi ah iyo amin leh qaababka steric modified.

Daraasada farsamada heterocyclic, Sidaa darteed, waxay diiradda saaraan inta badan derajooyinka aan codka lahayn iyo codsiyada waxaa ku jira shanta shan iyo sidoo kale lixda xubnood ee xubinta ka ah. Tan waxaa ka mid ah furan, pyrrole, thiophene, iyo pyridine. Fasalka weyn ee xeryaha heterocyclic waxaa lagu farsameeyaa qoryaha benzene, taas oo loogu talagalay furan, pyrrole, thiophene, iyo pyridine waa benzofuran, indole, benzothiophene, iyo quinoline, siday u kala horreeyaan. Haddii laba lakab oo benzene ah la isku daro, tani waxay keentaa qoys kale oo badan oo xeryahooda ah, kuwaas oo dibenzofuran, carbazole, dibenzothiophene, iyo aridine. Qalabka aan la faanin ayaa lagu kala saari karaa iyada oo ku saleysan ka qaybgalka heteroatom ee nidaamka pi, nidaamka isku dhafan.

Diyaarinta iyo falcelinta

Xatooyo 3 ah

Xeryahooda Heterocyclic oo leh saddex jajab ee giraangirta ayaa ah habab badan oo lafdhabar u ah cadaadiska giraanta. Heterocycles oo ku jira hal heteroatom ayaa guud ahaan deggan. Kuwa ka kooban laba heteroatom ayaa dhacaya, guud ahaan sida dhexdhexaadin ah.

Oxiranes, oo loo yaqaanno epoksides ayaa ah kuwa ugu badan ee 3-xubno heterocycles. Oxiranes waxaa loo diyaariyaa iyadoo la falceliyo xakamaynta alkenes, oo leh hab-dhaqan wanaagsan. Oxiranes way ka reebi karan marka loo eego anshaxyada aan la jecleysan ee xajmiga xagalka sare ee giraanta xubinta 3. Isku darka jawaab-celinta ka socota nucleophilic iyo furitaanka elektrofirafiga ee giraanta ayaa ah heerka ugu sarreeya ee fal-celinta.

Falcelinta noocan ah waxay ku lug leedahay daroogada nitrogen 'ficil-ka-daaweynta' kaas oo ka mid ahaa dawooyinka ugu horreeya ee daawada loo yaqaan 'antifancer'. Xiritaanka giraanta hurgunka ah sida kiiska mechlorethamine ee wakiilka antsancerine wuxuu sameeyaa daawada yariridium dhexdhexaad ah. Wakiilka firfircoon ee firfircoon wuxuu weeraro unugyo badan oo ay ku jiraan unugyada kansarka iyada oo loo marayo xannibaadda DNA-da. Noodhada yar-yar ee loo yaqaan 'nitrogen' ayaa sidoo kale loo isticmaalay wakiilada anticancer.

Ganacsi ahaan aziridiin iyo oxirane waa kiimikooyin badan oo warshad leh. Iibsiga mugdiinka weyn ee wax soo saarka, etylene wuxuu si toos ah uga jawaab celiyaa oksijiinka. Waxyeellada kiimikada, oo ah sifooyinka ugu badan ee ka mid ah siddooyinkan 3-xubinta, waxay tahay inay u nugul yihiin weerarka by reagentiy nucleophilic si ay u furaan giraanta sida hoos ku tusay:

Saddexda xubnood ee ugu caansan xeryahooda heterocyclic hal heteroatom waxaa ka mid ah:

Daacadnimo Bannaan la'aan
Thiirane (episulfides) Thiirene
Phosphirane Phosphirene
Epoxide (oksirane, oxideedka ethylene) Oxirene
Aziridiin Azirine
Borirane Borirene

Qaybaha ugu caansan ee heterosyclic ee leh saddex heteroatom ah waxaa ka mid ah Diaziridine oo ah nooc derivate ah iyo Diazirine oo ah nooc ka mid ah walxaha aan haboonayn iyo sidoo kale Dioxirane iyo Oxaziridine.

Qalabka afaraad ee xayeysiinta ah

Qaabab kala duwan oo loo diyaariyo siddeed xarig oo 4 ah ayaa lagu muujiyey jaantuska hoose. Nidaamka ka jawaab celinta amin, thiol ama 3-halo leh saldhig caadi ahaan waa mid waxtar leh, laakiin waxay keeneysaa dhexdhexaadin dhexdhexaad ah. Dermiyeynta iyo ka takooriddu waa falcelinta cilladda caadiga ah. Hawlaha kale ayaa sidoo kale ku tartamaya falcelinta.

Tusaale ahaan, isbeddelka loo yaqaan 'oxirane' wuxuu mar walba la tartamayaa dhismaha thetane, laakiin nukleophilicity sare ayaa ku sarreysa gaar ahaan haddii uu isticmaalo saldhig daciif ah.

Tusaale labaad, abuurista labada azetidiin iyo aziridiin waa suurtogal, laakiin kaliya marka dambe ayaa la arkaa. Tusaalaha lambarka afraad wuxuu muujinayaa in habkan loo sameeyo qaab-dhismeedka azetidiin si fiican u shaqeynayo haddii aysan jirin tartan.

Tusaalaha saddexaad, habka adag ee dhismaha substrate ee dhismaha oxetane oo ka hortagaya isbeddelka oxirane. Tusaalooyinka 5 iyo 6, daabacaadda Paterno-Buchi ayaa si gaar ah ugu habboon dhismaha oxetane.

Siyaabaha loo diyaarinayo xarigaha 4 ee xubin ka ah heterocycles

Falcelin

Racfaanada 4-xubin ka ah xeryahooda heterocyclic sidoo kale waxay muujineysaa saameynta cadaadiska giraanta. Jaantuska soo socda ayaa muujinaya tusaalooyin qaar. Xinjirta acid-ka waa habka caadiga ah ee fal-celinta kala duwan ee furan ee lagu soo bandhigay tusaalayaal 1,2, iyo 3a. Diidmada 2 ee thietane, sulfur waxay ku dhacdaa koloriin-dheere-dheereedka taasoo keenta in la sameeyo dhexdhexaadinta chlorosulfonium iyo beddelidda chloride iyio oo furan. Dareenka 3b, Nucleophiles xoog leh ayaa sidoo kale loo arkaa inay furto qulqulatada culus. Daawooyinka Beta-lactones 'waxaa laga yaabaa in ay dhacdo midba midka isdhex gareeya oo isbeddel ah sida lagu arkay 4a. Waxa kale oo ay dhici kartaa alwaax-O duufaan by nucleophiles sida 4b.

Tusaale nambar 6 wuxuu muujinayaa dhacdo xiiso leh oo dib-u-habeyn ah oo qeexaya habka loo yaqaan 'ester-ester'. Xogta 6 waxay muujinaysaa beta-lactam xakameynta penicillin G kaas oo sharxaya fal-celinta maqnaanshaha ee kor loo qaadey ee habka faleebada fused.

Tusaalooyinka jawaab-celinta xeryahooda 4 ee xubinta ka ah heterocyclic

Ugu faa'iido badan xeryahooda heterocyclic iyada oo xarigyada 4 ay ka kooban yihiin laba taxane ah oo antibiyootiko ah, cephalosporins, iyo penicillins. Labada taxane ah waxaa ku jira giraanta azetidinone oo sidoo kale loo yaqaanno Beta-lactam.
Qodobo badan oo loo yaqaan 'oxetanes' ayaa lagu baarayaa sida fayruska, daaweeyaha, antibacterment, iyo wakiilada antifungal. Oxetanones, dhinaca kale, ayaa inta badan lagu dabaqaa beeraha sida bactericides, fungicides, iyo herbicides iyo soo saarista polymer.
Weyne Wetane ayaa laga helay saliida shaleeshka iyada oo walxaha derisku ka shaqeeyaa ay u shaqeeyaan calaamad muujinaysa calaamadaha yurubiyanka ah ee loo yaqaan 'eurostats', lowska, iyo madow. Thietanes waxaa loo adeegsadaa sidii fungicides iyo bakteeriyada rinjiga, sida korontada ka hortagga birta, iyo soo saarista polymers.

Qeybaha afaraad ee xayeysiinta ah waxay kudhexaadaa hal heteroatom

Heteroatom Fadlan Lahayn

Heteroatom Daacadnimo Bannaan la'aan
Sulfur Thietane Azete
ogsijiin Oxetane Oxete
nitrogen Azetidiin Azete

Afartan xubnood ayaa xeryahooda ku leh laba heteroatom

Heteroatom Daacadnimo Bannaan la'aan
Sulfur Dithietane Dithiete
ogsijiin Dioxetane Dioxete
nitrogen Diazetidine Diazete

5-ka xubnood ee xubin ka ah hal heteroatom

Thiophene, furan, iyo pyrrole waa xeryaha aromatic ee waalidka ee 5-xubnihiisa kudoodaya heterocycles. Waa kuwan dhismooyinka:

Weedhada deriska ee tiyophene, furan, iyo pyrrole waa tiiophane, tetrahydrofuran, iyo pyrrolidin siday u kala horreeyaan. Xeryaha baaskiiliga ee ka sameysan tiyophene, furan, ama giraanta giraangirta ah ee loo yaqaan beneene benzene waxaa loo yaqaanaa benzothiophene, benzofuran, isoindole (ama indole).
Nitrogen heterocycle pyrrole waxa uu caadi ahaan ku dhacaa saliidaha lafaha oo lagu sameeyay qallafinta borotiinka iyadoo loo marayo kuleyl xoog leh. Sifaha pyrrole waxaa laga helaa astaamaha amino sida hydroxyproline iyo proline oo ah qaybo ka mid ah borootiinnada kala duwan ee ku jira heerarka sarreeya ee borotiinka qaabdhiska ah ee seedaha, tendinka, maqaarka, iyo lafaha iyo kolajka.
Pyrrole derivatives waxaa laga helaa alkaloids. Nikotiin waa kan ugu caansan ee loo yaqaan pyrrole oo ku jira alkaloid. Hemoglobin, myoglobin, Vitamin B12, iyo chlorophylls, ayaa dhamaantood la sameeyay iyagoo ku biiraya afar qaybood oo lafa-dabool ah oo ku jira nidaam weyn oo loogu yeero porphyrin, sida chlorophyll B hoos ku muujiyey.

Miisaanka laftirka ayaa la sameeyaa iyada oo loo marayo qallafsanaanta giraanta porphyrine iyo haysashada silsilad ah Xatooyo 4.
Diyaarinta qalabka hoomada ee 5 xubinta ka ah
Diyaarinta warshadaynta furan ee furan sida hoos ku tusay habka aldehyd, furfural, oo laga soo saaro pentose oo ka kooban walxo cayriin sida dhagaxyada. Diyaargaro isku mid ah oo ah tiyophene iyo pyrrole ayaa lagu muujiyay safka labaad ee isla'egyada.
Safka sadexaad ee isku midka ah mid ayaa muujinaya diyaarinta guud ee siyophenes beddelay, pyrroles, furans ka xeryahooda 1,4-dicarbonyl. Dareemooyin kale oo badan oo keenaya in la dhiso heterocycles beddelay noocyadan ayaa la bilaabay. Laba ka mid ah nidaamyadan ayaa lagu muujiyay falcelinta labaad iyo saddexaad. Furan waxaa yareeya hodbaadaha palladium-catalyzed hydrogenation si tetrahydrofuran. Eerkani waa mid qiimo leh oo aan loo beddeli karin 4-haloalkylsulfonates laakiin sidoo kale 1,4-dihalobutanes oo loo isticmaali karo si loogu diyaariyo kiyooloji iyo pyrrolidine.

Qeybaha shanaad ee xayeysiiska ah ee leh hal heteroatom

Heteroatom Bannaan la'aan Daacadnimo
Antimoni Stibole Stibolane
arsenic Arsole Arsolane
Bismuth Bismole Bismolane
Boron Borole Borolane
nitrogen Pyrrole Pyrrolidine
ogsijiin furan Tetrahydrofuran

5-xubno ka tirsan xubnaha 2 heteroatoms

Qaybaha shanaad ee xubnaha ah ee ku jira 2 heteroatoms iyo ugu yaraan mid ka mid ah heteroatomka waa Nitrogen, waxaa loo yaqaan 'azoles'. Isothiazoles iyo thiazoles ayaa ku jira khadadka nitrogen iyo sulfur atom. Isku dhafan oo leh laba xabbo oo sulfur ah ayaa loo yaqaan Dithiolanes.

Heteroatom Bannaan la'aan (iyo qayb ahaan aan la daboolin) Daacadnimo
nitrogen

/ nitrogen

Pyrazole (Pyrazoline)

Imidazole (Imidazolin)

Pyrazolidine

Imidazolidine

Nitrogar / Ooge Isoxazole

Oxazoline (oxazole)

Isoxazolidine

oxazolidine

Nitrogen / Sulfur Isotiazole

Thiazoline (Thiazole)

Isothiazolidine

Thiazolidine

Oksijiin / ogsijiin Dioxolane
Sulfur / sulfur Dithiolane

Qaar ka mid ah pyrazoles ayaa dabiiciyan ah. Qaybaha fasalkan waxaa loo diyaariyaa iyadoo la falgalayo 1,3-diketones leh hydrazines. Inta badan xeryahooda pyrazole ayaa loo isticmaalaa daawo iyo dhaylo. Waxaa ka mid ah xummad-yareereynin aminopyrin, fenybutazone oo loo isticmaalo daaweynta arthritis-ka, dharka fareebka iyo tartiib tartiib tartiib ah oo cunno cunno ah, iyo badanaaba maadada loo isticmaalo sawirrada midab-qabadka sida kuwa dareensan.

5-xubno ka tirsan xubnaha 3 heteroatoms

Waxaa sidoo kale jira kooxo badan oo ah xeryo shan xubnood leh oo leh ugu yaraan 3 heteroatoms. Hal tusaale oo ka mid ah xeryahooda sida dithiazoles kuwaas oo ku jira aaloji nitrogen iyo laba xabbo.

6 xubin ka ah xubnaha 1 heteroatom

Naqshadeynta loo adeegsado xayawaanka ku jira 6 ee xubnaha xashiishka leh ee monocyclic waa halkan hoose. Mowjadaha ku jira giraanta loogu talagalay pyridine ayaa lagu muujiyay, tirooyinka carabiga ayaa aad uga door biday xarfaha Giriiga, inkastoo labadaba loo isticmaalay. Pyridones waa maadooyin aromatic ah oo laxiriira qaybo ka mid ah iskudhafyada isdabajooga ee foomamka loo yaqaan "Resonance forms" sida lagu muujiyey 4-pyridone.

Laba shaybaar oo waaweyn oo ku lug leh falgalada dheef-shiid kiimikaad ee muhiimka ah ee unugyada, NAD (oo loo yaqaan coenzyme1) iyo NADP (oo loo yaqaan 'coenyme II'), ayaa laga soo qaatay nicotinamide.
Inta badan alkaloids waxay ku jiraan dhismaha dhererka loo yaqaan "piperidine" ama "pyridine ring", oo ka mid ah piperine (waxay ka dhigan tahay mid ka mid ah waxyaabaha kooban ee bacda madow iyo caddaanka ah) iyo nicotin. Qaab dhismeedyadooda ayaa hoos lagu muujiyay.

Pyridine oo markii hore laga soo saaro dhuxul laakin waxaa hadda loo diyaariyey ammonia iyo tetrahydrofurfuryl khamriga waa mid dhexdhexaad ah oo culeys loo isticmaalo si loo soo saaro xeryahooda kale. Vinylpyridines waa dhismayaal monomer muhiim ah ee balaastikada, iyo tuberidiin buuxa ee saturated, pyridine waxaa loo isticmaalaa walxo kiimiko ah iyo processing caag ah.

Pyridines oo faa'iido leh daawooyinka

Pharmaceutical pyridines (Pharmaceutical Pyrididine Pharmaceuticals) waxaa ka mid ah daawada isoniaotinic acid hydroxide (tuberculostat isoniazid), daawada ka hortagga AIDS-ka ee loo yaqaan nevirapine, nicorandil - avasodilator loo isticmaalo xakameynta angina, phenazopyridine-xanuunka kaadimareenka iyo sidoo kale daroogada sulfa ee anti-inflammatory. Diflufenican, clopyralid, paraquat, iyo diquat waa ciriiri pyridine deris ah oo loo isticmaalo sida herbicides.

6-xubno ka tirsan xubnaha 2 ama heteroatoms badan

3 monocyclic lixda xubnood ee heterocycles ee leh 2 nitrogen heteroatoms (diazines) ayaa lagu tiriyaa oo lagu magacaabo sida hoos ku qoran.

Nooca Hooyo Xayawaanku waa pyridazine derivative loo isticmaalo sida geedo. Dabagalka qaarkood sida aspergillic acid ayaa dabiiciyan ah. Halkaan waxaa ah qaababka ka mid ah xeryaha kor ku xusan:

Giraanta Pyrazine waa qayb ka mid ah xeryahooda kala duwan ee warshadaha kala duwan ee warshadaha iyo bayoolojiga. Xubnaha muhiimka ah ee qoyska pyrazine ayaa ah falada, alloxazines, iyo pteridines. Farmashiyaha iyo baayolojiga, diazonka ugu muhiimsan waa pyrimidines. Cytosine, thymine, iyo uracil waa 3 oo ah saldhigyada nucleotide 5 kaas oo ah qaabka hidaha ee RNA iyo DNA. Hoos waxaa ku yaal dhismayaashooda:

Vitamin thiamin waxay leedahay giraanta pyrimidine iyo marka lagu daro barbiturates oo ay ku jiraan amobarbital ayaa inta badan loo isticmaalaa daawooyinka. Morpholine (waalidiinta tetrahydro-1,4-oxazine) waxaa lagu soo saaraa qiyaas balaadhan oo loo isticmaalo sida fungicide, korontada ka hortagga, iyo dareeraha. Giraanta Morpholine ayaa sidoo kale laga helaa daawada loo yaqaan 'hypnotic trimetozine and some fungicides sida fenpropimorph iyo tridemorph. Waa kuwan qaab-dhismeedka qaab-dhismeed ee morpholine:

Xatooyo 7 ah

Iyada oo xajmiga sigaarku uu kordho, noocyada kala duwan ee xeryahooda oo laga yaabo in la helo iyada oo la beddelayo meesha, nooca, iyo tirada heteroatomka waxay kordhinaysaa si weyn. Si kastaba ha noqotee, kiimikada heterocycles ee leh 7-ka xubin ka ah ama ka badan ayaa ka hooseeya tan ka mid ah 6 iyo 5-xubinada xayndaabka heterocyclic.
Oxepine iyo Azepine ayaa ah kuwa ugu muhiimsan ee ka soo baxa waxyaalaha kala duwan ee dabiiciga ah ee ka yimaada noolaha badda iyo alkaloids. Wadeegta yarepine waxaa loo yaqaan 'caprolactam' oo loo yaqaan 'caprolactam' oo loo yaqaan 'caprolactam', waxaa lagu iibiyaa qashin badan si loogu isticmaalo wax soo saarka naylon-6 sida dhexdhexaad ah iyo soosaarka maqaar-dabiiciga ah, dharka, iyo filimada.
Xumoodka heterocyclic 7 oo leh laba ama mid ka mid ah atomiga nitrogen ee ku jira giraangiradooda waa qaybo qaab-dhismeed oo ah daaweynta nafsiga ah ee Prazepine (tricyclic antidepressant) iyo diazepam tranquilizer oo loo yaqaanno valium.

Xatooyo 8 ah

Tusaalooyinka noocyada heterocyclic ee fasalkan waxaa ka mid ah azocane, oxocane, iyo thiocane oo leh Nitrogen, oksijiin, iyo sulfur oo ah heteroatomada udhaxeeya. Wareegtooyinkooda aan loo baahnayn waa kuwa yar-yar, oxocin, iyo thiocine.

Xatooyo 9 ah

Tusaalooyinka noocyada heterocyclic ee fasalkan waxaa ka mid ah azonane, oxonane, iyo thionane oo leh Nitrogen, oksijiin, iyo sulfur oo ah heteroatomada udhaxeeya. Wareegyadooda kala duwan ee aan u baahneyn waa kuwa loo yaqaan 'azonine', oxonine, iyo thionine.

Isticmaal xeryahooda heterocyclic

Heterocycles waxay faa'iido u leedahay dhowr qaybood oo ah cilmiga nolosha iyo tiknoolajiyada. Sidii aan hore u aragay doodeena, daroogooyinka badani waa xeryahooda heterocyclic.

tixraacyada

IUPAC Gold Book, xeryahooda heterocyclic. Link:

WH Powell: Dib u eegida Nidaamka Hantzsch-Widman ee Nomenclature ee Heteromonocycles, ee: Pure Appl. Chem.1983, 55, 409-416;

A. Hantzsch, JH Weber: Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe), ee: Ber. Dtsch. Chem. Ges. 1887, 20, 3118-3132

O. Widman: Zur Nomenclatur der Verbindungen, welche Stickstoffkerne oo dhan, ee: J. Prakt. Chem. 1888, 38, 185-201;