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Maselo Oterewa Ambiri Mu Dziko Lonse

Maselo Oterewa Ambiri Mu Dziko Lonse

Makina ochepa

Chipinda cha heterocyclic, chomwe chimadziwikanso kuti mphete, chimakhala chigawo chokhala ndi maatomu a zinthu ziwiri zosiyana ndi ziwalo zake. Mankhwala otchedwa Heterocyclic mwina ndi omwe amapezeka mosiyanasiyana komanso omwe amapezeka kwambiri mumtundu wa mankhwala.

Mosasamala kanthu kogwira ntchito ndi mapangidwe, galimoto iliyonse ya carbocyclic ingasandulike mafananidwe osiyanasiyana a heterocyclic mwa kungotengera ma atomu a mpweya umodzi kapena kuposerapo. Chotsatira chake, maheterocycles apereka nsanja kuti apeze kafukufuku m'madera osiyanasiyana kuphatikizapo osagwiritsidwa ntchito kwa mankhwala, mankhwala, zowonongeka, ndi zamagetsi zokhala ndi mankhwala opha tizilombo.

Zitsanzo zazikulu za mankhwala a heterocyclic ndiwo mankhwala ambiri, nucleic acids, mitundu yambiri yamakono komanso yachilengedwe, komanso mitundu yambiri ya zamoyo monga cellulose ndi zipangizo zina.

gulu

Ngakhale kuti mankhwala amtundu wa heterocyclic angakhale organic kapena mankhwala, ambiri amakhala ndi carbon imodzi. Mafakitalewa akhoza kusankhidwa malinga ndi makina awo apakompyuta. Mafakitale amtundu wa heterocyclic amachititsa zinthu mofanana ndi zochokera ku acyclic. Zotsatira zake, tetrahydrofuran ndi piperidine ndizovomerezeka zotchedwa ethers ndi amines omwe ali ndi mbiri yosinthidwa.

Kuphunzira za chilengedwe cha heterocyclic, kotero, chimagwiritsidwa ntchito makamaka pa zotsalira zosagwedezeka ndi ntchito zomwe zimaphatikizapo mphete zisanu zosasunthika komanso zisanu ndi chimodzi. Izi zikuphatikizapo furan, pyrrole, thiophene, ndi pyridine. Gulu lalikulu lotsatira la mankhwala a heterocyclic akuphatikizidwa ndi mphete za benzene, zomwe zimapanga furan, pyrrole, thiophene, ndi pyridine ndi benzofuran, indole, benzothiophene, ndi quinoline. Ngati mphete ziŵiri za benzeni zikuphatikizidwa, izi zimapangitsa banja lina lalikulu la mankhwala, omwe ali dibenzofuran, carbazole, dibenzothiophene, ndi aridine. Mphete zosasinthika zingathe kusankhidwa pogwiritsa ntchito heteroatom mu pi system, conjugated dongosolo.

Kukonzekera ndi kusintha

Zingwe za 3

Heterocyclic yokhala ndi ma atomu atatu mu mphete ndi njira yowonjezereka yogwirizana ndi vuto la mphete. Ma heterocycles okhala ndi heteroatom imodzi amakhala osakhazikika. Zomwe zili ndi heteroatom ziwiri zimachitika, makamaka ngati zowonongeka.

Oxiranes, omwe amadziwikanso kuti epoxides ndi amphongo ambiri omwe amapezeka m'thupi la 3. Oxiranes amakonzedwa pochita ma peracids ndi zizindikiro, ndi zochitika zabwino. Oxiranes ndi otetezeka kwambiri kuposa ma ethers osatetezedwa omwe amayamikira kwambiri mapepala a 3. Zowonjezeredwa zomwe zimachitika ndi khungu lokhala ndi magetsi ndi electrophilic kutsegula kwa mpheteyi ndilo gulu lachidziwitso.

Kuchita kwa mtundu umenewu kumaphatikizapo ntchito ya mankhwala a mphutsi yomwe imakhala imodzi mwa mankhwala oyambirira a antiticancer. Kutsekedwa kwa mphete ya intramolecular monga momwe zimakhalira ndi wothandizira ziwalo mechlorethamine amapanga mazira a pakati pa aziridium ion. Wopanga biologically yogwira ntchito amachititsa maselo ochulukirapo kuphatikizapo maselo a khansa kupyolera mu kulepheretsa kubwereza kwawo kwa DNA. Mavitomu a mpiru amagwiritsidwanso ntchito ngati antiticancer agents.

Malonda aziridine ndi oxirane ndizofunikira kwambiri mankhwala. Pochita kupanga kwambiri oxirane, ethylene imayendetsedwa mwachindunji ndi mpweya. Mankhwalawa, omwe amadziwika kwambiri ndi mphete za 3, ndizoti amatha kugwidwa ndi ziwalo zogwiritsira ntchito mankhwalawa kuti azitsegula mphete monga momwe ili pansipa:

Ambiri omwe ali ndi ziwalo zitatu mankhwala ochepa ndi heteroatom imodzi ndi awa:

Wokhutira Osatulutsidwa
Thiirane (episulfides) Thiirene
Phosphirane Phosphirene
Limapangidwanso (oxirane, ethylene oxide) Oxirene
Aziridine Azioni
Borirane Borirene

Mankhwala atatu omwe amapezeka pamtundu wa heterocyclic ndi ma heteroatom awiri amadziwika ndi Diaziridine monga chochokera ndi Diazirine monga mankhwala osatulutsidwa komanso Dioxirane ndi Oxaziridine.

Mapulogalamu Amodzi Anayi

Njira zosiyanasiyana zokonzekera ziwalo zamphongo zamkati za 4 zikuwonetsedwa mu chithunzi chomwe chili pansipa. Njira yothetsera amine, thiol kapena 3-halo yomwe ili ndi maziko amathandiza makamaka koma ndi zokolola zochepa. Kuchepetsa ndi kuwonongeka ndizochitika pambali. Ntchito zinanso zingapikisane nawo.

Mu chitsanzo choyamba, kupanga njinga kwa oxirane nthawi zonse kumapikisana ndi mapangidwe a thietane, koma mtima wapamwamba umakhala makamaka makamaka ngati wina amagwiritsa ntchito zofooka.

Mu chitsanzo chachiwiri, mapangidwe a azote aziti ndi aziridine amatha, koma okhawo amatha kuwonekera. Chitsanzo chachinayi chikuwonetsa kuti njira iyi yopanga azetidine imayenda bwino ngati palibe mpikisano.

Mu chitsanzo chachitatu, kugwiritsidwa ntchito kolimba kwa gawoli kumapanga mapangidwe a oxetane ndipo kumateteza cyclization ya oxirane. Mu zitsanzo 5 ndi 6, zithunzi za Paterno-Buchi photocyclizations zimayenera makamaka kupanga mapangidwe a oxetane.

Njira yokonzekera mphete za 4 mphete zapakhungu

Zotsatira

Zochita za ma 4 mankhwala ochepa Onetsani zowonongeka. Chithunzi chotsatira chikuwonetsa zitsanzo. Acid-catalysis ndichizoloŵezi chosiyanasiyana cha machitidwe oyang'aniridwa mu zitsanzo 1,2, ndi 3a. Zomwe zimachitika 2 ya thietane, sulufule imayendetsedwa ndi electrophilic chlorination yomwe imayambitsa chlorosulfonium pakati ndikuikapo chloride ion. Pochita 3b, nucleophiles amphamvu amawonanso kuti atsegule ether. Machitidwe a cletavage a Beta-lactones angachitike mwina ndi asidi-catalyzed acyl kusiyana monga momwe taonera mu 4a. Zingathenso kuchitidwa ndi al-O-kupasuka ndi nucleophiles monga 4b.

Chitsanzo cha nambala 6 chikuwonetseratu chidwi chokhazikitsanso kachilombo ka ortho-ester. Zochitika 6 imasonyeza Beta-lactam cleavage ya penicillin G yomwe imalongosola njira yowonjezeredwa yowonjezeredwa ya dongosolo la mphete.

Zitsanzo za zochitika za mankhwala a 4 a heterocyclic mankhwala

Zothandiza kwambiri mankhwala ochepa ndi mphete za 4 ndi awiri a antibiotic, cephalosporins, ndi penicillins. Mapepala awiriwa ali ndi mphete ya azetidinone yomwe imatchedwanso Beta-lactam ring.
Ng'ombe zambiri zimayang'aniridwa ngati mankhwala osokoneza bongo, antiticancer, anti-inflammatory, and antitifungal agents. Ma oxetanoni, makamaka, amagwiritsidwa ntchito mu ulimi monga bactericides, fungicides, ndi herbicides komanso kupanga polima.
Mayi thietane anapezeka mu mafuta a shale pamene zovuta zake zowopsya zimagwira ntchito ngati zonunkhira za European polecats, ferrets, ndi minks. Thietanes amagwiritsidwa ntchito monga fungicides ndi baktericides mu utoto, monga zitsulo zotentha zitsulo, komanso popanga ma polima.

Mphindi zinayi zimakhala ndi heteroatomu imodzi

Heteroatomu Yokhutira Yosasinthika

Heteroatom Wokhutira Osatulutsidwa
Sulfure Thietane Azete
Oxygen Oxetane Oxete
asafe Azetidine Azete

Mphete zamphongo zinayi zimaphatikizapo heteroatoms iwiri

Heteroatom Wokhutira Osatulutsidwa
Sulfure Dithietane Dithiete
Oxygen Dioxetane Dioxete
asafe Diazetidine Diazete

Mphindi ya 5 ndi heteroatom imodzi

Thiophene, furan, ndi pyrrole ndizozizira zonunkhira zazing'ono zamphongo za 5. Nazi zinthu zawo:

Zotsatira zokhudzana ndi thiophene, furan, ndi pyrrole ndi thiophane, tetrahydrofuran, ndi pyrrolidine mofanana. Bicyclic mankhwala opangidwa ndi thiophene, furan, kapena pyrrole mphete yomwe imagwiritsidwa ntchito ku ringeni ya benzene amadziwika kuti benzothiophene, benzofuran, isoindole (kapena indole).
Mavitamini a heterocycle pyrrole amapezeka m'mafupa omwe amapangidwa ndi kuwonongeka kwa mapuloteni kudzera mu kutentha kwakukulu. Mapuloteniwa amapezeka mu amino acid monga hydroxyproline ndi proline omwe ali zigawo za mapuloteni osiyanasiyana omwe ali pamwamba pa mapuloteni a mitsempha, matope, khungu, mafupa ndi collagen.
Zokwanira zapiritsi zimapezeka mu alkaloids. Nicotine ndi pyrrole yodziŵika kwambiri yomwe ili ndi alkaloid. Hemoglobin, myoglobin, Vitamini B12, ndi chlorophylls, zonse zimapangidwa mwa kujowina magulu anayi a pyrrole m'dongosolo lalikulu la mphete lotchedwa porphyrin, monga ya chlorophyll B yomwe ili pansipa.

Kuyika ma piritsi kumapangidwira kuwonongeka kwa mphete ya porphyrine ndipo muli ndi makina a 4 pyrrole mphete.
Kukonzekera kwa ziwalo za 5 zamphongo zapakhosi
Kukonzekera kwa mafakitale kumatuluka monga momwe tawonetsera m'munsi mwa njira ya aldehyd, furfural, yomwe imachokera ku pentose yomwe ili ndi zipangizo monga chimanga. Kukonzekera komweku kwa thiophene ndi pyrrole kumawonetsedwa mzere wachiwiri wa equation.
Mzere wachitatu wa equation wina amasonyeza kukonzekera kwambiri kwa thiophenes, pyrroles, furans kuchokera ku 1,4-dicarbonyl mankhwala. Zochitika zambiri zambiri zomwe zimatsogolera kupanga mapangidwe a ntchentche zamtundu umenewu zapangidwa. Njira ziwiri mwazinthuzi zasonyezedwa muchiwiri ndi chachitatu. Furan imachepetsedwa ndi palladium-catalyzed hydrogenation ku tetrahydrofuran. Ether imeneyi ndi yothandiza kwambiri yomwe imangotembenuzidwa kukhala 4-haloalkylsulfonates komanso 1,4-dihalobutanes yomwe ingagwiritsidwe ntchito pokonzekera thiolane ndi pyrrolidine.

Mphete zisanu ndi ziwiri zimakhala ndi heteroatom imodzi

Heteroatom Osatulutsidwa Wokhutira
Antimoni Sungani Stibolane
Arsenic Arsole Arsolane
Bismuth Bismole Bismolane
Boron Borole Borolane
asafe Piritsi Pyrrolidine
Oxygen Furan Tetrahydrofuran

Mphindi ya 5 ndi 2 heteroatoms

Mitundu ya makina asanu yomwe ili ndi heteroatom ya 2 ndipo imodzi mwa heteroatoms ndi azitrogeni, yotchedwa azoles. Isothiazoles ndi thiazoles ali ndi atomu ya nayitrogeni ndi sulfa m'kati mwake. Mavitamini ndi maatomu awiri a sulfure amadziwika kuti Dithiolanes.

Heteroatom Unsaturated (ndi pang'ono unsaturated) Wokhutira
asafe

/ nayitrogeni

Pyrazole (Pyrazoline)

Imidazole (Imidazoline)

Pyrazolidine

Imidazolidine

Asitrogeni / mpweya Isoxazole

Oxazoline (oxazole)

Isoxazolidine

oxazolidine

Asitrogeni / sulufule Isothiazole

Thiazoline (Thiazole)

Isothiazolidine

Thiazolidine

Oxygen / mpweya Dioxolane
Sulfure / sulufule Dithiolane

Ena a pyrazoles amapezeka mwachibadwa. Mapangidwe a kalasiyi akukonzekera pochita 1,3-diketoni ndi hydrazines. Mankhwala ambiri a pyrazole amagwiritsidwa ntchito monga mankhwala ndi dyes. Zimaphatikizapo kuchepetsa kutentha kwa malungo aminopyrine, phenybutazone yogwiritsidwa ntchito pa mankhwala a nyamakazi, utoto wa tebulo ndi chikasu cha mtundu wa tartrazine, komanso mitundu yambiri ya utoto yomwe imagwiritsa ntchito kujambula zithunzi ngati othandizira.

Mphindi ya 5 ndi 3 heteroatoms

Palinso gulu lalikulu la mphete zisanu zomwe zimapangidwa ndi 3 heteroatoms. Chitsanzo chimodzi cha mankhwala amenewa ndi dithiazoles omwe ali ndi atomu ya nitrojeni ndi sulfure ziwiri.

Mphindi ya 6 ndi 1 heteroatom

Dzina lakuti nomenclature limene limagwiritsidwa ntchito mumadzimadzi a mchere wa 6 omwe ali ndi nitrojeni ndi awa pansipa. Malo okhala pamphete ya pyridine amasonyezedwa, ziwerengero za Chiarabu zimakonda kwambiri makalata achi Greek, ngakhale zida zonsezo zikugwiritsidwa ntchito. Pyridones ndi mankhwala okometsera owongoledwa ndi zopereka zowonongeka ndi mafomu osungirako katundu monga momwe anawonetsera 4-pyridone.

Zida ziwiri zazikuluzikulu zomwe zimagwira ntchito zosiyanasiyana m'magulu, NAD (yomwe imatchedwa coenzyme1) ndi NADP (yomwe imatchedwanso coenyme II), imachokera ku nicotinamide.
Ambiri a alkaloids ali ndi piperidine kapena pyridine ring structure, pakati pawo piperine (amapanga chimodzi mwa zolawa chakuthwa chakuda wakuda ndi tsabola woyera) ndi chikonga. Nyumba zawo zikuwonetsedwa pansipa.

Pyridine yomwe idatulutsidwa kuchokera ku phula lamakala koma tsopano yokonzedwa catalytically kuchokera ku ammonia ndi tetrahydrofurfuryl mowa ndizofunikira kwambiri ndi zosungunulira zomwe zimagwiritsidwa ntchito popanga mankhwala ena. Vinylpyridines ndi mapuloteni ofunikira kwambiri, ndipo piperidine, pyridine yodzaza ndi zinthu zambiri zimagwiritsidwa ntchito monga mankhwala opangira mankhwala ndi mphira.

Mankhwala othandizira mankhwala

Mankhwala omwe amagwiritsidwa ntchito ndi mankhwala ndi isonicotinic acid hydrazide (tuberculostat isoniazid), mankhwala osokoneza bongo omwe amadziwika ndi nevirapine, nicorandil - avasodilator omwe amagwiritsidwa ntchito polamulira angina, phenazopyridine-mankhwala odzola m'mitsempha komanso mankhwala osokoneza bongo. Diflufenican, clopyralid, paraquat, ndi diquat ndi zotchuka kwambiri za pyridine zomwe zimagwiritsidwa ntchito monga mankhwala a herbicides.

Mphindi ya 6 ndi 2 kapena heteroatoms

Mankhwala a 3 opangidwa ndi maselo asanu ndi limodzi omwe amatha kupangira matumbo otchedwa 2 nitrogen heteroatoms (diazines) amalembedwa ndipo amatchulidwa monga pansipa.

Maleic hydrazide ndi chochokera ku pyridazine chomwe chimagwiritsidwa ntchito monga herbicide. Ma pyrazines ena monga aspergillic acid amapezeka mwachilengedwe. Nazi ziganizo za mankhwala omwe tatchulawa:

Mzere wa Pyrazine ndi mbali ya mitundu yambiri ya polycyclic ya mafakitale ndi zamoyo. Mamembala ofunika a banja la pyrazine ndi phenajini, alloxazines, ndi pteridines. Pharmacologically ndi biologically, chofunika kwambiri diazines ndi pyrimidines. Cytosine, thymine, ndi erracil ndi 3 yazitsulo za 5 zomwe zimapanga ma genetic mu RNA ndi DNA. M'munsimu muli nyumba zawo:

Vitamini thiamin ali ndi mphete ya pyrimidine komanso kuwonjezera pa kupanga mankhwala omwe amobarbital amagwiritsa ntchito mankhwala osokoneza bongo. Morpholine (kholo tetrahydro-1,4-oxazine) amapangidwa pamtunda waukulu kuti agwiritsidwe ntchito monga fungicide, kutupa mpweya, ndi zosungunulira. Mphete ya Morpholine imapezekanso mu mankhwala osokoneza bongo a trimetozine ndi zina zotchedwa fenicpimorph ndi tridemorph. Pano pali dongosolo la morpholine:

Zingwe za 7

Pamene kukula kwa mphete kumawonjezereka, mitundu yosiyanasiyana ya mankhwala yomwe ingapeze posiyanitsa malo, mtundu, ndi nambala ya heteroatoms ikuchuluka kwambiri. Komabe, zimapangidwe zamakono ndi ma pulogalamu a 7 kapena zambiri sizinapangidwe kusiyana ndi za 6 ndi 5-ring ring heterocyclic compounds.
Mapepala a Oxepine ndi Azepine ndizofunikira kwambiri za mitundu yosiyanasiyana ya zamagetsi zamadzi ndi alkaloids. Chombo chotchedwa azepine chotchedwa caprolactam chimagulitsidwa malonda kwambiri kuti chigwiritsidwe ntchito popanga nylon-6 monga pakati ndi kupanga zopangidwa, zikopa, ndi mafilimu.
Mankhwala a 7 a heterocyclic mankhwala ndi atomu awiri kapena amodzi a nayitrojeni mu mphete zawo ndi zigawo zomangidwa ndi psychopharmacealticals Prazepine (tricyclic anti-stress) ndi tranquilizer diazepam amadziwika kuti valium.

Zingwe za 8

Zitsanzo za mankhwala otchedwa heterocyclic mu kalasiyi zikuphatikizapo azocane, oxocane, ndi thiocane ndi nayitrogeni, oksijeni, ndi sulfure kukhala heteroatoms. Zotsatira zawo zosasinthika ndizo azocine, oxocine, ndi thiocine.

Zingwe za 9

Zitsanzo za mankhwala otchedwa heterocyclic mu kalasiyi zikuphatikizapo azonane, oxonane, ndi thionane ndi nayitrogeni, oksijeni, ndi sulfure ndi heteroatoms. Zotsatira zake zosatulutsidwa ndi azonine, oxonine, ndi thionine mofanana.

Zochita za mankhwala otchedwa heterocyclic

Maheketeroni amathandiza m'madera angapo a sayansi ya moyo ndi zamakono. Monga momwe taonera kale, mankhwala ambiri ndi mankhwala ophwanyidwa.

Zothandizira

IUPAC Gold Book, mankhwala opha tizilombo toyambitsa matenda. Lumikizani:

WH Powell: Kukonzanso kwa njira yotchedwa Hantzsch-Widman System of Nomenclature ya ma Homerococycles, mu: Appl yoyera. Chem.1983, 55, 409-416;

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

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