Получение и масс-спектрометрический анализ 5,6- дигидро-4H-пирроло[3,2,1-ij]хинолин-1,2-диона и 1,1'- (1,2-диоксоэтан-1,2-диил)бис-1,2,3,4- тетрагидрохинолина
Ключевые слова:
1,2,3,4-тетрагидрохинолин, оксалилхлорид, масс-спектрометрия, колоночная хроматография, 5,6-дигидро-4H-пирроло[3,2,1-ij]хинолин-1,2-дион, 1,1'-(1,2-диоксоэтан- 1,2-диил)бис-1,2,3,4-тетрагидрохинолин.
Аннотация
Методом колоночной хроматографии выделены индивидуальные продукты взаимодействия
1,2,3,4-тетрагидрохинолина с оксалилхлоридом - 5,6-дигидро-4H-пирроло[3,2,1-ij]хинолин-1,2-дион и
1,1'-(1,2-диоксоэтан-1,2-диил)бис-1,2,3,4-тетрагидрохинолин, подобраны эффективные элюирующие
смеси. Идентификацию и подтверждение структуры полученных соединений осуществляли методом
масс-спектрометрии, определены основные направления фрагментации.
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Литература
1. Morales-Ramos.A.I., Mecom J.S., Kiesow
T.J., Graybill T.L., Brown G.D. et al.
Tetrahydro-4-quinolinamines identified as
novel P2Y1 receptor antagonists, Bioorganic &
Medicinal Chem. Letters, 2008, No. 18, pp.
6222-6226.
2. Shono T., Matsumura Y., Inoue K.,
Ohmizu H., Kashimura Sh. Electroorganic
chemistry reaction of iminium ion with
nucleophile: a versatile synthesis of
tetrahydroquinolines and julolidines, J. Am.
Chem. Soc., 1982, No. 104, pp. 5753-5757.
3. Perry N.B., Blunt J.W., Munro M.H.G.
Cytotoxic pigments from new zealand sponges
of the genus latrunculia : discorhabdins a, b and
c, Tetrahedron, 1988, No. 44, pp. 1727-1734.
4. Miyoshi M., Morisaki N., Tokiwa Y.,
Kobayashi H., Iwasaki S. et al. Facile reductive
rearrangement of dynemicin a to dynemicin H:
the direct evidence for the p-phenylene
diradical intermediate, Tetrahedron Lett,. 1991,
No. 32, pp. 6007-6010.
5. Wender P. A., Beckham S., Mohler D.L.
The intramolecular addition of silylated alkynes
to aldehydes: Methodology for the construction
of cyclic enediynes and its application to
dynemicin analogs, Tetrahedron Lett, 1995, No.
36, pp. 209-212.
6. Witherup K.M., Ransom R.W., Graham
A.C., Bernard A.M., Salvatore M.J. et al.
Martinelline and martinellic acid, novel Gprotein
linked receptor antagonists from the
tropical plant Martinella iquitosensis
(Bignoniaceae), J. Am. Chem. Soc., 1995, No.
117, pp. 6682-6685.
7. Gracheva I.N., Gridneva L.I., Tochilkin
A.I., Gorkin V.Z. Hydrazides and sulfonyl
hydrazides from the series of quinoline are
human serum amine oxidase inhibitors, Khim.-
Farm. Zh. 1988, No. 22, pp. 1336-1339.
8. Youssefyeh R.D., Magnien E., Lee T.D.Y.,
Chan W.K., Lin C.J. et al. Development of a
novel series of (2-quinolinylmethoxy)phenylcontaining
compounds as high-affinity
leukotriene receptor antagonists. 1. Initial
structure-activity relationships, J. Med. Chem.,
1990, No. 33, pp. 1186-1194.
9. Pooley Ch.L., Edwards J.P., Goldman
M.E., Wang M-W, Marschke K.B et al.
Discovery and Preliminary SAR Studies of a
Novel, Nonsteroidal Progesterone Receptor
Antagonist Pharmacophore, J. Med. Chem.,
1998, No. 41, pp. 3461-3466.
10. El Tahir K.E.H., Al-Kharji A.M.H., Ageel
A.M. Effect of praziquantel and oxamniquine
on prostacyclin synthesis by the rat arterial and
myometrial tissues, Gen. Pharmac, 1992, No.
23, pp. 131-139.
11. Omura S., Nakagawa A. Structure of
virantmycin, a novel antiviral antibiotic ,
Tetrahedron Lett., 1981, No. 22, pp. 2199-2202.
12. Williamson N.M., March D.R., Ward
A.D. An improved synthesis of 2,2-
disubstituted-1,2-dihyroquinolines and their
conversion to 3-chloro-2,2-disubstitutedtetrahydroquinolines
, Tetrahedron Lett., 1995,
No. 36, pp. 7721-7724.
13. Kasaikina O.T., Kartasheva Z.S.,
Lobanova T.V. Osobennosti ingibirovaniya
okisleniya uglevodorodov gidrirovannymi khinolinami, Neftekhimiya. 1982, T. 22, No 2,
pp. 265-271.
14. Kasaikina O.T., Lobanova T.V., Fentsov
D.V. Mekhanizm ingibirovaniya protsessov
okisleniya uglevodorodov 2,2,4-trimetil-6-oksi-
1,2,3,4-tetragidrokhinolinom, Izv. AN SSSR.
Ser. khim., 1983, No. 10, pp. 2212-2218.
15. Tikhonov V.P., Zaveshchevskaya T.L.,
Sidlyarov D.P. Antioksidantnyi i
antigipoksantnyi kompleks na osnove
digidrokvertsetina dlya kosmeticheskikh izdelii,
pat. PCT/RU2009/000192 RF: WO
2009134165 A1. 05.11.2009.
16. Rozantsev E.G., Gagarina A.B.,
Kasaikina O.T. Ivanov Yu.A., Shapiro A.B.
Oksiproizvodnye-2,2,4-trimetil-1,2,3,4-tetragidrokhinolina,
kak antioksidanty dlya
karotinoidov i sposob ikh polucheniya , pat. SU
№ 548603. 28.023.77
17. Egorov I.A., Gulyushin S.Yu., Kovalev
V.O. Sposob stabilizatsii kombikormov , pat.
RF № 2329659. 27.07.2008.
18. Medvedeva S.M., Krysin M.Yu., Zubkov
F.I., Nikitina E.V., Shikhaliev Kh.S. Novye
geterotsiklicheskie sistemy na osnove
zameshchennykh 3,4-digidro-1Nspiro[
khinolin-2,1'-tsikloalkanov], Khimiya
geterotsiklicheskikh soedinenii, 2014, No. 9,
pp. 1388-1399.
19. Leshcheva E.V., Medvedeva S.M.,
Shikhaliev Kh.S. Sintez 4,4,6-trimetil-8-R-4Hpirrolo[
3,2,1-ij]khinolin-1,2-dionov , Zhurnal
organіchnoї ta farmatsevtichnoї khіmії, 2014,
No. 12, pp. 15-20.
20. Medvedeva S.M., Shikhaliev Kh.S.,
Leshcheva E.V., Solov'ev A.S. 4,4,6-Trimetil-
4H-pirrolo[3,2,1-ij]khinolin-1,2-diony v
reaktsiyakh tsiklokondensatsii s binukleofilami,
Vestn. Voronezh. gos. un-ta. Ser. Khimiya.
Biologiya. Farmatsiya, 2005, No. 2, pp. 54-59.
21. Medvedeva S.M., Shikhaliev Kh.S.,.
Sanina G.S, Solov'ev A.S. 4,4,6-Trimetil-1,2-
digidro-4H-pirrolo[3,2,1-ij]khinolin-1,2-diony
v trekhkomponentnykh reaktsiyakh
kondensatsii , Butlerovskie soobshcheniya,
2006, No 7, pp. 37-40.
22. Kojima E., Fujimori Sh., Awano K.
Cyclic anthranilic acid derivatives and process
for their preparation , pat. 5147874 US: Kyorin
Pharmaceutical Co., Ltd. 15.09.1992.
23. Kojima E., Saito K. Therapeutic agents of
metabolic bone disease , pat. EP 0402859 B1:
Kyorin Pharmaceutical Co., Ltd. 12.06.1990
24. Crumrine D.S., Dieschbourg T.A.,
O'Toole J.G., Tassone B.A., Vandeburg S.C.
Sodium Metal Promoted Condensations of
Carbamates, J. Org. Chem., 1987, No. 52, pp. 3699-3701.
25. Zhungietu G. I., Rekhter M. A. Izatin i
ego proizvodnye , Kishinev: Shtiintsa, 1977, 228 p.
26. Takhistov V.V. Prakticheskaya massspektrometriya
organicheskikh soedinenii , L.:
Izd-vo Leningr. un-ta, 1977, 268 p.
T.J., Graybill T.L., Brown G.D. et al.
Tetrahydro-4-quinolinamines identified as
novel P2Y1 receptor antagonists, Bioorganic &
Medicinal Chem. Letters, 2008, No. 18, pp.
6222-6226.
2. Shono T., Matsumura Y., Inoue K.,
Ohmizu H., Kashimura Sh. Electroorganic
chemistry reaction of iminium ion with
nucleophile: a versatile synthesis of
tetrahydroquinolines and julolidines, J. Am.
Chem. Soc., 1982, No. 104, pp. 5753-5757.
3. Perry N.B., Blunt J.W., Munro M.H.G.
Cytotoxic pigments from new zealand sponges
of the genus latrunculia : discorhabdins a, b and
c, Tetrahedron, 1988, No. 44, pp. 1727-1734.
4. Miyoshi M., Morisaki N., Tokiwa Y.,
Kobayashi H., Iwasaki S. et al. Facile reductive
rearrangement of dynemicin a to dynemicin H:
the direct evidence for the p-phenylene
diradical intermediate, Tetrahedron Lett,. 1991,
No. 32, pp. 6007-6010.
5. Wender P. A., Beckham S., Mohler D.L.
The intramolecular addition of silylated alkynes
to aldehydes: Methodology for the construction
of cyclic enediynes and its application to
dynemicin analogs, Tetrahedron Lett, 1995, No.
36, pp. 209-212.
6. Witherup K.M., Ransom R.W., Graham
A.C., Bernard A.M., Salvatore M.J. et al.
Martinelline and martinellic acid, novel Gprotein
linked receptor antagonists from the
tropical plant Martinella iquitosensis
(Bignoniaceae), J. Am. Chem. Soc., 1995, No.
117, pp. 6682-6685.
7. Gracheva I.N., Gridneva L.I., Tochilkin
A.I., Gorkin V.Z. Hydrazides and sulfonyl
hydrazides from the series of quinoline are
human serum amine oxidase inhibitors, Khim.-
Farm. Zh. 1988, No. 22, pp. 1336-1339.
8. Youssefyeh R.D., Magnien E., Lee T.D.Y.,
Chan W.K., Lin C.J. et al. Development of a
novel series of (2-quinolinylmethoxy)phenylcontaining
compounds as high-affinity
leukotriene receptor antagonists. 1. Initial
structure-activity relationships, J. Med. Chem.,
1990, No. 33, pp. 1186-1194.
9. Pooley Ch.L., Edwards J.P., Goldman
M.E., Wang M-W, Marschke K.B et al.
Discovery and Preliminary SAR Studies of a
Novel, Nonsteroidal Progesterone Receptor
Antagonist Pharmacophore, J. Med. Chem.,
1998, No. 41, pp. 3461-3466.
10. El Tahir K.E.H., Al-Kharji A.M.H., Ageel
A.M. Effect of praziquantel and oxamniquine
on prostacyclin synthesis by the rat arterial and
myometrial tissues, Gen. Pharmac, 1992, No.
23, pp. 131-139.
11. Omura S., Nakagawa A. Structure of
virantmycin, a novel antiviral antibiotic ,
Tetrahedron Lett., 1981, No. 22, pp. 2199-2202.
12. Williamson N.M., March D.R., Ward
A.D. An improved synthesis of 2,2-
disubstituted-1,2-dihyroquinolines and their
conversion to 3-chloro-2,2-disubstitutedtetrahydroquinolines
, Tetrahedron Lett., 1995,
No. 36, pp. 7721-7724.
13. Kasaikina O.T., Kartasheva Z.S.,
Lobanova T.V. Osobennosti ingibirovaniya
okisleniya uglevodorodov gidrirovannymi khinolinami, Neftekhimiya. 1982, T. 22, No 2,
pp. 265-271.
14. Kasaikina O.T., Lobanova T.V., Fentsov
D.V. Mekhanizm ingibirovaniya protsessov
okisleniya uglevodorodov 2,2,4-trimetil-6-oksi-
1,2,3,4-tetragidrokhinolinom, Izv. AN SSSR.
Ser. khim., 1983, No. 10, pp. 2212-2218.
15. Tikhonov V.P., Zaveshchevskaya T.L.,
Sidlyarov D.P. Antioksidantnyi i
antigipoksantnyi kompleks na osnove
digidrokvertsetina dlya kosmeticheskikh izdelii,
pat. PCT/RU2009/000192 RF: WO
2009134165 A1. 05.11.2009.
16. Rozantsev E.G., Gagarina A.B.,
Kasaikina O.T. Ivanov Yu.A., Shapiro A.B.
Oksiproizvodnye-2,2,4-trimetil-1,2,3,4-tetragidrokhinolina,
kak antioksidanty dlya
karotinoidov i sposob ikh polucheniya , pat. SU
№ 548603. 28.023.77
17. Egorov I.A., Gulyushin S.Yu., Kovalev
V.O. Sposob stabilizatsii kombikormov , pat.
RF № 2329659. 27.07.2008.
18. Medvedeva S.M., Krysin M.Yu., Zubkov
F.I., Nikitina E.V., Shikhaliev Kh.S. Novye
geterotsiklicheskie sistemy na osnove
zameshchennykh 3,4-digidro-1Nspiro[
khinolin-2,1'-tsikloalkanov], Khimiya
geterotsiklicheskikh soedinenii, 2014, No. 9,
pp. 1388-1399.
19. Leshcheva E.V., Medvedeva S.M.,
Shikhaliev Kh.S. Sintez 4,4,6-trimetil-8-R-4Hpirrolo[
3,2,1-ij]khinolin-1,2-dionov , Zhurnal
organіchnoї ta farmatsevtichnoї khіmії, 2014,
No. 12, pp. 15-20.
20. Medvedeva S.M., Shikhaliev Kh.S.,
Leshcheva E.V., Solov'ev A.S. 4,4,6-Trimetil-
4H-pirrolo[3,2,1-ij]khinolin-1,2-diony v
reaktsiyakh tsiklokondensatsii s binukleofilami,
Vestn. Voronezh. gos. un-ta. Ser. Khimiya.
Biologiya. Farmatsiya, 2005, No. 2, pp. 54-59.
21. Medvedeva S.M., Shikhaliev Kh.S.,.
Sanina G.S, Solov'ev A.S. 4,4,6-Trimetil-1,2-
digidro-4H-pirrolo[3,2,1-ij]khinolin-1,2-diony
v trekhkomponentnykh reaktsiyakh
kondensatsii , Butlerovskie soobshcheniya,
2006, No 7, pp. 37-40.
22. Kojima E., Fujimori Sh., Awano K.
Cyclic anthranilic acid derivatives and process
for their preparation , pat. 5147874 US: Kyorin
Pharmaceutical Co., Ltd. 15.09.1992.
23. Kojima E., Saito K. Therapeutic agents of
metabolic bone disease , pat. EP 0402859 B1:
Kyorin Pharmaceutical Co., Ltd. 12.06.1990
24. Crumrine D.S., Dieschbourg T.A.,
O'Toole J.G., Tassone B.A., Vandeburg S.C.
Sodium Metal Promoted Condensations of
Carbamates, J. Org. Chem., 1987, No. 52, pp. 3699-3701.
25. Zhungietu G. I., Rekhter M. A. Izatin i
ego proizvodnye , Kishinev: Shtiintsa, 1977, 228 p.
26. Takhistov V.V. Prakticheskaya massspektrometriya
organicheskikh soedinenii , L.:
Izd-vo Leningr. un-ta, 1977, 268 p.
Опубликован
2019-11-20
Как цитировать
Medvedeva, S. M., Shikhaliev, K. S., Kryl’skii, D. V., & Siniaeva, L. A. (2019). Получение и масс-спектрометрический анализ 5,6- дигидро-4H-пирроло[3,2,1-ij]хинолин-1,2-диона и 1,1’- (1,2-диоксоэтан-1,2-диил)бис-1,2,3,4- тетрагидрохинолина. Сорбционные и хроматографические процессы, 14(6). извлечено от https://journals.vsu.ru/sorpchrom/article/view/1581
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