SU320484A1 - The method of obtaining gamma - [(6-mercaptopuryl) -alpha-benzyl-N-carbobenzoxy] -L-glutamic acid - Google Patents
The method of obtaining gamma - [(6-mercaptopuryl) -alpha-benzyl-N-carbobenzoxy] -L-glutamic acidInfo
- Publication number
- SU320484A1 SU320484A1 SU1258438A SU1258438A SU320484A1 SU 320484 A1 SU320484 A1 SU 320484A1 SU 1258438 A SU1258438 A SU 1258438A SU 1258438 A SU1258438 A SU 1258438A SU 320484 A1 SU320484 A1 SU 320484A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- glutamic acid
- benzyl
- carbobenzoxy
- mercaptopuryl
- alpha
- Prior art date
Links
- -1 6-mercaptopuryl Chemical group 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004220 glutamic acid Substances 0.000 description 4
- 229960001428 mercaptopurine Drugs 0.000 description 4
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 3
- 229960002989 Glutamic Acid Drugs 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 240000002840 Allium cepa Species 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N Dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 230000002427 irreversible Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 235000002732 oignon Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Description
Изобретение относитс к снособам получени нового, не описанного в л ггературс соединени , нредставл ющего собой сложный эфир 6-меркаптопурина и L-глутаминовой кислоты. Такие вещества вл ютс необратимыми ингибиторами ферментов и могут найти применение в качестве новых лекарственных препаратов.The invention relates to methods for the preparation of a compound not described in the laboratory, which is a 6-mercaptopurine ester and L-glutamic acid. Such substances are irreversible enzyme inhibitors and can be used as new drugs.
В литературе описан способ получени -(6-меркаптонурил)-а-г/ ег-бутил-Н - карбобензокси -Ь-глутаминоБой кислоты .M конденсации 6-меркаптонурина и a-r/;er-6yTii,iЫ-карбобензокси-Ь-глутаминовой кислоты.The literature describes a method for producing - (6-mercaptonuryl) -a-g / er-butyl-H - carbobenzoxy-l-glutamic acid. M condensation of 6-mercaptonurine and ar /; er-6yTii, iY-carbobenzoxy-b-glutamic acid .
Недостатком этого метода вл етс сравнительно невысокий (24%) выход целевого продукта.The disadvantage of this method is the relatively low (24%) yield of the target product.
Цель изобретени - получение соединени на основе 6-меркаптопурина и -бензилЫ-карбобензокси-Ь-глутаминовой кислоты с высоким выходом дл того, чтобы можно было создать промышленные схемы.The purpose of the invention is to obtain a compound based on 6-mercaptopurine and -benzyl carbo-benzoxy-b-glutamic acid in high yield so that industrial schemes can be created.
С этой целью использован карбодиимидный метод, нримен емый в синтезе пептидов. Однако дл синтеза соединений оннсаипого выше нового класса карбодиимидный метод пспользуетс впервые.For this purpose, the carbodiimide method used in the synthesis of peptides was used. However, the carbodiimide method is used for the first time to synthesize compounds of onions above a new class.
с сс-бензил-Х-карбобспзокси-Ь - глутамнновой кислотой Б присутствии М,К-дицикло1ексилкарбодиимида в дпметилфор.мамнде. Выход целевого продукта 57-59%.with cc-benzyl-X-carboxy benzyl-b - glutamic acid B in the presence of M, C-dicyclo-hexylcarbodiimide in dimethylformamn. The yield of the target product 57-59%.
Полученные соединени отличаютс от известных типом заместител .The compounds obtained are different from those known by the type of substituent.
Пример. К раствору 1 г (2,7 ммоль) абензил-Х-карбобензокс 1-1 .-глутаминовой кислоты в 5 м. диметилформамида добавл ют 0,4 г (2,7 м. 6-меркаптопурина и 0,56 г (0,27 ммоль) Х,1Ч-днциклогексилкарбодииМИДа . Через 24 lac (20°С) отдел ют осадок дициклогексилмочевины, а маточный раствор выливают в 100 мл охлажденного до -5°С сухого эфира. Дл очистки выпавшее вещество дважды пеоеосаждают.Example. To a solution of 1 g (2.7 mmol) of abenzyl-X-carbobenzox 1-1.-Glutamic acid in 5 m of dimethylformamide, 0.4 g (2.7 m. Of 6-mercaptopurine and 0.56 g (0, 27 mmol) X, 1H-dicyclohexylcarbodiaMIDA After 24 lac (20 ° C), the dicyclohexylurea precipitate was separated, and the mother liquor was poured into 100 ml of dry ether cooled to -5 ° C. To purify the precipitated substance twice, precipitate twice.
Выход 57%, т. пл. 204-206°С (с разл.), УФ-спектр: Л:,:акс. 221,5 (е 17600, ацетонитрил ).Yield 57%, so pl. 204-206 ° C (with decomp.), UV spectrum: L:,: ax. 221.5 (e 17600, acetonitrile).
Найдено, %: С 58,82; Н 4,70; S 6,33.Found,%: C 58.82; H 4.70; S 6.33.
Вычислено, %: С 59,41; Н 4,55; S 6,14.Calculated,%: C 59.41; H 4.55; S 6.14.
П р с д м с т и 3 о б р е т е и и P r with d m with m and 3 about the breach and and
Способ получени -(б-меркаптопури.) -а1 М1:;1:;;- .- арбобензокс1:-1,-1лут;п1И1ЮВОй кислоты , отличающийс тем, что 6-меркаптопурин подвергают взаимодействию с а-бензилХ-карбобе}13уТ с11-Ь-глутамииовой кислотой в присутствии Х ,К|-дициклогексилкарбодии.мида в диметилформамиде.The method of preparation is (b-mercaptopuri.) -A1 M1:; 1: ;; - .- arbobenzox 1: -1, -1 flut; p1I1; IVO acid, characterized in that the 6-mercaptopurine is reacted with a-benzylX-carboxy} 13 T T 11 -L-glutamic acid in the presence of X, K | -dicyclohexylcarbodia.mide in dimethylformamide.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU320484A1 true SU320484A1 (en) | 1971-11-04 |
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