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Mafi yawan Hannun Hanya a Duniya

Mafi yawan Hannun Hanya a Duniya

Hanyoyin Hotorocyclic

Gidaran heterocyclic, wanda aka fi sani da tsarin zobe yana da mahimmanci fili wanda ya ƙunshi nau'o'in abubuwa biyu masu rarrabe kamar mambobi na zobe / zobba. Ma'aikata masu amfani da kwayoyin halitta sun kasance mafi yawan bambancin kuma yawancin masu yawan kwayoyin halitta.

Duk da aiki da tsari, duk wani shinge na carbocyclic zai iya canzawa zuwa wasu analogs heterocyclic ta hanyar maye gurbin ɗaya ko fiye da ƙwayoyin ƙarar ƙwayar ƙwayar murya tare da nau'in daban-daban. A sakamakon haka, heterocycles sun miƙa wani dandamali ga musayar bincike a fannoni daban daban ciki har da amma bai iyakance don pharmaceutical, magani, hikimar tantance, kuma Organic sunadarai na heterocyclic mahadi.

Misalan misalai na mahadar heterocyclic sune mafi yawan kwayoyi, kwayoyin nucleic acid, yawancin kayan ado da kayan duniyar halitta, da kuma yawancin kwayoyin halittu irin su cellulose da kayan da suka danganci.

Nau'in

Kodayake mahaɗin heterocyclic na iya kasancewa kwayoyin halitta ko marasa tsari, mafi yawan suna da akalla ɗaya carbon. Wadannan mahadi zasu iya rarraba bisa ga tsarin lantarki. Magungunan heterocyclic masu yawa suna nuna hali kamar yadda acyclic ƙayyade. A sakamakon haka, tetrahydrofuran da piperidine sune masu yaduwa ne da kuma amines tare da bayanan martaba da aka gyara.

Nazarin ilimin kimiyyar heterocyclic, sabili da haka, ya mayar da hankali kan abubuwan da ba a samarda su ba kuma aikace-aikacen sun shafi unstrained biyar da lambobin da aka ƙaddara su shida. Wannan ya hada da furan, pyrrole, thiophene, da pyridine. A na gaba manyan aji na heterocyclic mahadi da aka Fused zuwa benzene zobba, wanda for Furan, pyrrole, thiophene, kuma pyridine ne benzofuran, indole, benzothiophene, kuma quinoline, bi da bi. Idan an yi amfani da zoben benzene guda biyu, wannan zai haifar da wani babban iyali na mahadi, wanda shine dibenzofuran, carbazole, dibenzothiophene, da kuma maganin aridine. Za'a iya rarraba zobba ba tare da ƙaddara ba a cikin ɓarna a cikin tsarin pi, tsarin tsarin.

Shiri da halayen

3-membered zobba

Magungunan haɗi da ke da nau'o'i uku a cikin zobe sune mafi dacewa da karfin siginar zobe. Hannun da ke dauke da daya heteroatom suna ci gaba. Wadanda ke dauke da kwayoyin cutar guda biyu suna faruwa, a matsayin maɗamaiyar tsaka-tsaki.

Oxiranes, wanda aka fi sani da suna epoxides sune mafi girma na 3-membered heterocycles. Oxiranes suna shirya ta hanyar yin magana da haka tare da alkenes, tare da kyakkyawan yanayin da yake da shi. Oxiranes sun fi maida hankali fiye da ladaran da aka yi da unsherrated ethers na babban kuskuren nauyin nauyin 3-membered. Ƙarin haɓakawa da ke gudana ta hanyar haɓaka na nucleophilic da electrophilic na zobe sune mafi yawan nau'in jituwa.

Irin wannan nau'i yana da nasaba da aikin nitrogen na dole ne a cikin kwayar halittar kwayoyin halitta wadda ta kasance daga cikin farkon kwayoyin maganin anticancer. Rufe murfin ƙirar kamar ƙwayar wakili na anticancer mechlorethamine ya samar da wani nau'in aziridium na tsakiya. Magunguna wadanda suka hada da kwayar cutar ta hanyar haɓaka kwayoyin halitta ta hanyar yada kwayoyin halittar DNA. An yi amfani da ƙwayoyin Nitrogen har zuwa matsayin agents anticancer.

Dabiridine da oxirane na kasuwanci suna da muhimmanci sunadaran masana'antu. A kan yaduwar samari na oxirane, ethylene an kai tsaye tare da oxygen. Sakamakon sinadaran, wanda shine mafi yawan halayen wadannan nau'ikan 3-membered, shine cewa suna iya iya kaiwa hari daga mahalarophilic reagents don buɗe sautin kamar yadda aka nuna a kasa:

Mafi na kowa uku membered heterocyclic mahadi tare da daya heteroatom sun hada da:

M Ba a sani ba
Thiirane (episulfides) Saurin
Phosphirane Phosphirene
Epoxides (oxirane, ethylene oxide) Oxirene
Aziridine Azirine
Borirane Borirene

Mafi yawan kwayoyin heterocyclic da aka haɗo da ƙwayoyin cuta guda biyu sun hada da Diaziridine a matsayin mai dadi da kuma Diazirine a matsayin mai ba da kyauta da Dioxirane da Oxaziridine.

Four-Membered Zobba

Ana nuna hanyoyi daban-daban na shirye-shirye na nau'i na 4-membered a cikin zane a kasa. Hanyar amsawa da amine, thiol ko 3-halo tare da tushe yana da mahimmanci amma tare da karuwar mediocre. Dimension da kawarwa sune halayen halayen halayen. Wasu ayyuka kuma zasu iya yin gasa a cikin karfin.

A cikin misali na farko, yin amfani da cygiler zuwa wani oxirane ko da yaushe ya yi jihadi tare da samfurin thietane, amma mafi girma nucleophilicity rinjaye musamman idan mutum yana amfani da tushe mara ƙarfi.

A misalin na biyu, za'a iya samun azetidine da aziridine, amma kawai ana ganin su. Misali na lamba huɗu ya nuna cewa wannan tsarin kula da azetidine yana aiki da kyau idan babu gasa.

A cikin misalin na uku, ƙaddamarwar sanyi na maɓallin da ke da ƙarancin kafawar oxetane kuma yana hana cyclization na oxirane. A cikin misalai 5 da 6, hotunan Paterno-Buchi sun dace da samin oxetane.

Hanyoyi na shirya 4-membered ƙugiyoyi masu tsauri

halayen

Ayyukan 4-membered heterocyclic mahadi Har ila yau, yana nuna rinjayar sautin. Zane mai zane yana nuna wasu misalai. Acid-catalysis wani nau'i ne na halayen haɓaka da aka nuna a misalai 1,2, da kuma 3a. A dauki 2 na thietane, sulfur shigarsu electrophilic chlorination kai ga samuwar chlorosulfonium tsaka-tsaki da kuma canza zobe-bude chloride ion. A yayin da 3b ke yin amfani da shi, ana ganin magungunan nucleophiles masu karfi don buɗe fili. Beta-lactones 'gyare-gyare halayen iya faruwa ko dai ta hanyar acid-catalyzed acyl musayar kamar yadda gani a 4a. Haka kuma zai iya faruwa ta hanyar alkyl-O rupture by nucleophiles kamar a 4b.

Misali na lamba 6 ya nuna wani abu mai ban sha'awa na sakewa na intramolecular na astho-ester. Ma'anar 6 ta nuna alamar Beta-lactam ta ɓoye na penicillin G wadda ke bayyana fasalin haɓakaccen haɓakaccen tsarin tsarin ƙaddamarwa.

Misalan halayen haɗin mahaɗin Xtexoxlic 4-membered

Mafi amfani heterocyclic mahadi tare da zoben 4-membered su ne jerin maganin maganin rigakafi guda biyu, da cephalosporins, da penicillin. Lissafin biyu sun ƙunshi nau'in azetidinone wanda aka sani da suna Beta-lactam.
Mutane da yawa suna binciken ne a matsayin bincike na antiviral, anticancer, anti-inflammatory, da kuma jami'in antifungal. Oxetanones, a gefe guda, an fi amfani da su a aikin noma kamar yadda kwayoyin cutar kwayoyin cuta, masu fadi, da kuma herbicides da kuma masana'antu na polymer.
An gano iyayensu a cikin man shale yayin da abubuwan da suka samo asali sunyi aiki a matsayin alamar turare ga ƙwararrun Turai, ƙuƙumi, da minks. Ana amfani da kwayoyin su a matsayin furotin da bactericides a cikin paintin, kamar yadda masu hana hakar gine-ginen ƙarfe, da kuma masana'antun polymers.

Ƙungiyar mahaɗan mahaɗi hudu da guda heteroatom

Heteroatom Mafi Girma

Hotoro M Ba a sani ba
sulfur Kayan Azete
oxygen Oxetane Oxete
nitrogen Azetidine Azete

Ƙungiyar zobe mai ƙididdigewa hudu tare da heteroatoms biyu

Hotoro M Ba a sani ba
sulfur Dithietane Dithiete
oxygen Dioxetane Dioxete
nitrogen Diazetidine Diazete

5-membered zobba tare da guda heteroatom

Thiophene, furan, da pyrrole sune mahaifa masu magungunan ƙananan nau'i na nau'in 5-membered. Ga tsarin su:

Abubuwa masu yawa na thiophene, furan, da pyrrole su ne thiophane, tetrahydrofuran, da pyrrolidine daidai da haka. Kwayoyin bicyclic da aka yi da zobe na thiophene, furan, ko pyrrole zuwa zane na benzene an san su da benzothiophene, benzofuran, isoindole (ko indole).
Kwayar kwayar cutar ta Nitrogen yawanci yakan faru ne a cikin man fetur da aka kafa ta hanyar bazuwar sunadarai ta hanyar zafi mai tsanani. Ana gano nau'ikan pyrrole a cikin amino acid irin su hydroxyproline da layi da suke da nau'o'in sunadarai daban-daban da ke gabatarwa a manyan ƙwayoyi a tsarin gina jiki na ligaments, tendons, fata, da kasusuwa da collagen.
An gano adadin pyrrole a cikin alkaloids. Nicotine ita ce mafi yawan sanannun pyrrole wanda ya ƙunshi alkaloid. Hemoglobin, myoglobin, Vitamin B12, da kuma chlorophylls, duk an kafa su ta hanyar shiga raka'a hudu na pyrrole a cikin babban sakonnin da ake kira porphyrin, kamar yadda aka nuna a chlorophyll B a ƙasa.

An kafa sinadarin Bile ta hanyar bazuwar zoben porphyrin kuma suna da sarƙoƙi na 4 pyrrole.
Shirin shirye-shiryen ƙwayoyin ƙarancin 5-membered
Shirye-shiryen masana'antu na Furan ya samu kamar yadda aka nuna a kasa ta hanyar aldehyd, furfural, wanda aka samo daga pentose wanda ya ƙunshi kayan yaji irin su corncobs. Anyi amfani da shirye-shirye na thiophene da pyrrole a jere na biyu na daidaito.
Hanya na uku na daidaito ɗaya yana nuna babban shiri na maye gurbin thiophenes, pyrroles, furan daga 1,4-dicarbonyl mahadi. Yawancin sauran halayen da suka haifar da samo irin wannan nau'i sun fara. Biyu daga cikin wadannan hanyoyin an nuna su a karo na biyu da na uku. Furan an rage shi ta hanyar palladium-catalyzed hydrogenation zuwa tetrahydrofuran. Wannan mai yaduwa ne mai mahimmanci wanda ba za'a iya canzawa kawai zuwa 4-haloalkylsulfonates amma kuma 1,4-dihalobutanes wanda za'a iya amfani dasu don shirya thiolane da pyrrolidine.

Ƙidodi biyar mai ɗaukar nauyin mahaifa da guda heteroatom

Hotoro Ba a sani ba M
Antimony Stibole Stibolane
arsenic Arsole Arsolane
Bismuth Bismole Bismolane
boron Borole Borolane
nitrogen Pyrrole Pyrrolidine
oxygen Furan Tetrahydrofuran

Ƙungiyar 5-membered da 2 heteroatoms

Kwayoyin ƙawanin ƙididdiga biyar waɗanda ke dauke da heteroatoms na 2 kuma a kalla daya daga cikin heteroatoms shine Nitrogen, wanda ake kira azoles. Isothiazoles da thiazoles suna da nitrogen da sulfur a cikin zobe. Magunguna da ƙwayoyin sulfur biyu suna da suna Dithiolanes.

Hotoro Ba a bayyana shi ba (kuma an ba shi sassauci) M
nitrogen

/ nitrogen

Pyrazole (Pyrazoline)

Imidazole (Imidazoline)

Pyrazolidine

Imidazolidine

Nitrogen / oxygen Isoxazole

Oxazoline (oxazole)

Isoxazolidine

oxazolidine

Nitrogen / sulfur Isothiazole

Thiazoline (Thiazole)

Isothiazolidine

Thiazolidine

Oxygen / oxygen Dioxolane
Sulfur / sulfur Dithiolane

Wasu pyrazoles suna faruwa a hankali. Ma'aikata na wannan aji suna shirya ta hanyar amsa 1,3-diketones tare da hydrazines. Ana amfani da yawancin mahadar pyrazole da aka yi amfani da su a matsayin magani da dyes. Sun hada da analgesic aminopyrin zazzabi, phenybutazone da ake amfani da su a maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin maganin jini, da yaduwar fiber da launin launi na launin rawaya, da kuma yawancin kayan ado da aka yi amfani da su a cikin launi na daukar hoto kamar yadda ake amfani da su.

Ƙungiyar 5-membered da 3 heteroatoms

Akwai kuma babban rukuni na mahaɗin haɗin mai ƙididdiga biyar da akalla XTUMX heteroatoms. Ɗaya daga cikin misalan irin wannan mahadar shine dithiazoles wanda ya ƙunshi nau'in nitrogen da sulfur biyu.

6-membered zobe tare da 1 heteroatom

Yankin nomenclature wanda ake amfani da shi a cikin ƙwayoyin zobe na 6-membered na monocyclic wanda ke dauke da nitrogen ne a nan kasa. An nuna matsayi a kan zoben don pyridine, ana nuna adadin Larabci a cikin haruffa Helenanci, kodayake ana amfani dasu biyu. Pyridones sune masu kyauta masu kyauta na gudummawar don samuwa daga kamfanonin resonance kamar yadda aka nuna ga 4-pyridone.

Ƙananan coenzymes masu yawa sun haɗa da wasu abubuwa masu mahimmanci a cikin kwayoyin halitta, NAD (wanda aka sani da coenzyme1) da kuma NADP (wanda aka sani da coenyme II), an samo daga nicotinamide.
Mafi yawan alkaloids sun ƙunshi tsarin piperidine ko tsarin pyridine, a cikin su na ciki (wanda ya zama daya daga cikin abubuwan da ke cikewa da baki) da kuma nicotine. An nuna su a ƙasa.

Pyridine wanda aka cire sau ɗaya daga tashar kwalba amma an riga an shirya shi daga cikin ammonia kuma tetraydrofurfuryl barasa ne muhimmin matsakaici da sauran ƙarfi da ake amfani dashi don gina wasu mahadi. Vinylpyridines suna da mahimmanci gine-ginen ginin ginin plastics, kuma cikakken cikakken piperidine, ana amfani da pyridine a matsayin kayan sunadarai da kayan aiki na roba.

Pharridceutically amfani pyridines

Amfani da pyridines masu amfani da kwayoyi sun hada da hydrazide isonicotinic acid (tuberculostat isoniazid), magungunan maganin cutar AIDS-virus da aka sani da nevirapine, nicorandil - avasodilator wanda ake amfani da shi wajen shan iska, phenazopyridine-maganin urinary-tracts da kuma maganin maganin rigakafi na maganin cutar. Diflufenican, clopyralid, paraquat, da kuma diquat sune abubuwan da ake kira pyridine wadanda aka yi amfani da ita azaman herbicides.

6-membered zobe tare da 2 ko fiye heteroatoms

3 monocyclic ƙididdigar ƙira guda shida tare da 2 nitrogen heteroatoms (diazines) an ƙidaya kuma sunaye kamar yadda aka nuna a kasa.

Maleic hydrazide ne mai amfani da pyridazine da aka yi amfani da shi azaman herbicide. Wasu pyrazines irin su aspergillic acid ke faruwa a yanayi. A nan ne sifofin maharan da aka ambata:

Ƙungiyar Pyrazine wata ƙungiya ce ta magungunan ƙwayoyin polycyclic na masana'antu da kuma muhimmancin rayuwa. Mahimman membobin iyali na pyrazine sune phenazines, allurazines, da pteridines. Dandalin magani da ilimin likitanci, zane-zane mafi muhimmanci shine pyrimidines. Cytosine, thymine, da uracil su ne 3 na sansanin nucleotide na 5 wadanda suka kasance code a cikin RNA da DNA. Da ke ƙasa akwai gininsu:

Vitamin thiamin yana da zoben pyrimidine kuma banda adadin barbiturates na roba ciki har da alamun da ake amfani da shi a cikin magunguna. Morpholine (iyaye tetrahydro-1,4-oxazine) an samo a kan babban sikelin don amfani azaman fungicide, mai hana lalata, da kuma sauran ƙarfi. Ana kuma samo sutin zubar da jini a cikin magungunan miyagun ƙwayoyi na tumuttuka da wasu masu fuka-fuka irin su fenpropimorph da tridemorph. Ga tsarin tsarin tsari na morpholine:

7-membered zobba

Kamar yadda girman zobe ya ƙaru, yawancin mahadi da za'a iya samuwa ta hanyar canzawa wuri, iri, da kuma yawan heteroatoms yana ƙaruwa ƙwarai. Duk da haka, ilimin sunadarai na kwayoyin da ƙananan nau'in 7-membered ko ƙari ba shi da ƙananan cigaba fiye da na 6 da 5-membered ring heterocyclic mahadi.
Oxepine da Azepine zobba suna da mahimmanci masu mahimmanci na wasu abubuwa masu lahani na halitta na kwayoyin halitta da alkaloids. Abinda aka gano azepine wanda aka sani da caprolactam an samar da shi ne a cikin ƙananan don yin amfani da shi wajen yin nylon-6 a matsayin matsakaici da kuma samar da fata, kayan ado, da fina-finai.
7-membered heterocyclic mahadi tare da biyu ko daya nitrogen nitrogen a cikin zobe ne sassan tsarin mai amfani da psychopharmaceuticals Prazepine (tricyclic antidepressant) da tranquilizer diazepam kuma da aka sani da valium.

8-membered zobba

Misalan mahaɗar heterocyclic a cikin wannan aji sun hada da azane, oxocane, da thiocane tare da Nitrogen, oxygen, da sulfur kasancewa da keraroatoms. Abubuwan da basu dace ba sune azocine, oxocine, da thiocine daidai da daya.

9-membered zobba

Misalan mahaɗar heterocyclic a cikin wannan aji sun hada da azonane, oxonane, da thionane tare da Nitrogen, oxygen, da sulfur kasancewa ne da ke dauke da heteroatoms. Abubuwan da basu dace ba sune azonine, oxonine, da thionine.

Amfani da magungunan heterocyclic

Hanyoyi suna da amfani a wurare da dama na kimiyya da fasaha. Kamar yadda muka riga muka gani a cikin tattaunawa, yawancin kwayoyi sune mahaɗar heterocyclic.

References

IUPAC Gold Book, heterocyclic mahadi. Linin:

WH Powell: Bisa ga tsarin Hantzsch-Widman da aka ƙaddara don ƙaddarar ƙira, a cikin: Tsarin Appl. Chem.1983, 55, 409-416;

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

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