2Uchinchi renessans yosh olimlari: zamonaviy vazifalar,
innovatsiya va istiqbol Young Scientists of the Third Renaissance: Current Challenges, Innovations and Prospects
TRISIKLIK 1H-1,2,3-TRIAZOL HOSILALARINING SINTEZI
Z. I. Murtazayeva -
kimyo kafedrasi tayanch doktoranti, X. A. Bozorov Organik sintez va bioorganik kimyo kafedrasi professori.
Samarqand davlat universiteti. Biokimyo instituti. zarifamurtazayeva92@gmail.com. O'zbekiston.
1,2,3-Triazol halqasi saqlagan geterosiklik birikmalar tibbiy kimyoda o'zining strukturaviy tuzilishi va xilma-xil biologik faolliklari bilan muhim ahamiyatga ega hisoblanadi. Besh a'zoli geterosiklik birikmalar orasida uchta azotli geteroatomga ega bo'lgan triazol birlamchi geterosiklik molekula bo'lib, birinchi marta 1885-yilda Bladdin tomonidan kashf etilgan. Ikkita n bog'i va elektron jufti tufayli u aromatik xususiyatga ega [1]. Metabolik degradatsiyaga, kislota-asos gidroliziga va qaytarilish-oksidlanishga chidamliligi uning aromatiklik xususiyatining natijasidir [2]. 1,2,3-Triazol halqasini o'z ichiga olgan gibrid birikmalar va tegishli geterosikllarning yetakchi birikmalari tibbiy kimyo sohasida saratonga qarshi, mikroblarga qarshi, silga qarshi, virusga qarshi, diabetga qarshi, bezgakka qarshi, leyshmaniyaga qarshi agentlar/nomzod birikmalar va neyroprotektiv vositalar yetarlicha topilgan [3-10] (1-rasm).
Tarkibida ekzosiklik aminoguruh saqlagan 1,2,3-triazollarning sintezi va kimyoviy xossalarini o'rganish so'nggi yillarda rivojlanib bormoqda. Buning asosiy sabablaridan biri aminoguruh yuqori reaksion qobiliyatga ega bo'lib, uning asosida turli elektrofil almashinish (alkillash, asillash va b.) reaksiyalarini o'rganish orqali turli yangi hosilalar olish mumkinligi, hamda yangi geteroxalqalar hosil qilish orqali potensial farmakologik moddalar sintez qilish mumkin.
Bizning tadqiqot guruhimiz etil sianoatsetat va bir necha xil fenil azidlar o'rtasidagi 1,3-dipolyar sikllanish reaksiyasi orqali 1^-1,2,3-triazollarning yangi hosilalarini sintez qildi va va ularning strukturaviy tahlillarini o'rgandi.
373
May 15, 2024
Uchinchi renessansyosh olimlari: zamonaviy vazifalar,
innovatsiya va istiqbol Young Scientists of the Third Renaissance: Current
Cha'Les.hnnoeon.andPru.en
/=0
HO
Tazobaktam, 1
N
N=N
Rufnamid, 2
9
NH,
K F
CK
.N. ö-
Mubritinib, 5
Karboksiamidotriazol, 7
1-rasm 1H-1,2,3-triazollar asosidagi dori vositalari
5-Amino-1-#-aril-1#-1,2,3-triazol etil efirlarining sintezini amalga oshirish uchun dastlabki modda sifatida anilin (1a), toluidin (1b) va 4-almashgan anilinlar (1c-j) tanlab olindi. Dastlab, anilin va uning hosilalari bilan natriy azidi, natriy nitrit hamda xlorid kislota ishtirokida 0-5 °C da 4 soat davomida xona haroratida magnit aralashtirgich yordamida aromatik elektrofil almashish reaksiyasi olib borildi. Olingan aril azidlar (2a-j) etil sianoatsetat bilan natriy etoksid ishtirokida xona haroratidan 40 °C gacha bo'lgan sharoitda inert atmosferada uch soat davomida aralashtirildi. Reaksiya aralashmasi 50 ml muzli suvga quyildi. Olingan hosil bo'lgan kristallar filtrlash orqali yig'iladi va mos ravishda triazol efirlari (3a-j) 56 dan 93% gacha bo'lgan yaxshi unum bilan hosil bo'ldi (2-rasm).
' NaN3, NaN02
HCl, 4 s
+
0^/CH3 C2H5ONa
rt-40°C
1a-j
2a-j
a: R=4-H b: R=4-Me
c: R=4-Et d: R=4-F
e: R=4-CI f: R=4-Br
g: R=4-OMe h: R=4-CF3
i: R=3,4-CI j: R=4-CN
2-rasm. 5-Amino-1-N-aril-1N-1,2,3-triazol etil efirlarining umumiy sintezi
1-Jadval. Yangi 5-amino-1-N-aril-1N-1,2,3-triazol etil efirlarining suyuqlanish harorati va hosil bo'lish unumlari:
R Moddalar Unumlar, % Suyuqlanish harorati, °C
4-H 3a 62 130-131
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May_15,_2024
Uchinchi renessans yosh olimlari: zamonaviy vazifalar,
innovatsiya va istiqbol Young Scientists of the Third Renaissance: Current Challenges, Innovations and Prospects
4-Me 3b 65 154-155
4-Et 3c 67 159-160
4-F 3d 60 130-131
4-Cl 3e 95 157-159
4-Br 3f 93 164-165
4-OMe 3g 90 145-146
4-CF3 3h 91 148-149
3,4-Cl 3i 82 128-130
4-CN 3j 75 140-141
Reaksiyaning ikkinchi bosqichi 5-amino-1-#-aril-W-1,2,3-triazol etil efirlari (3a-j) va 2-pirolidon (4) ning turli sharoitlarda POCl3 ishtirokida reaksiya sharoitlarini optimallashtirish orqali olib borildi va siklizatsiya mahsuloti bo'lgan 1,2,3-triazollarning yangi trisiklik hosilalari (5a-j) sintez qilindi (3-rasm).
POCI3i 1,4-flkiOKcaH
N
N
N "N
//
5a-j
a: R=4-H c: R=4-Et b: R=4-Me d: R=4-F
e: R=4-CI f: R=4-Br
g: R=4-OMe h: R=4-CF3
i: R=3,4-CI j: R=4-CN
3-rasm. Yangi 1#-1,2,3-tritsiklik triazol hosilalari sintezining umumiy sxemasi
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Uchinchi renessansyosh olimlari: zamonaviy vazifalar,
innovatsiya va istiqbol Young Scientists of the Third Renaissance: Current Challenges, Innovations and Prospects
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