RU2015101582A - Amides of N- (2-aminopurin-6-yl) -6-aminocaproic acid having antitumor activity, and a method for their preparation - Google Patents

Amides of N- (2-aminopurin-6-yl) -6-aminocaproic acid having antitumor activity, and a method for their preparation Download PDF

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RU2015101582A
RU2015101582A RU2015101582A RU2015101582A RU2015101582A RU 2015101582 A RU2015101582 A RU 2015101582A RU 2015101582 A RU2015101582 A RU 2015101582A RU 2015101582 A RU2015101582 A RU 2015101582A RU 2015101582 A RU2015101582 A RU 2015101582A
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aminopurin
amides
aminocaproic acid
antitumor activity
general formula
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RU2015101582A
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RU2599577C2 (en
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Виктор Павлович Краснов
Дмитрий Андреевич Груздев
Галина Львовна Левит
Евгений Николаевич Чулаков
Алексей Юрьевич Вигоров
Валерий Николаевич Даниленко
Вера Васильевна Мусияк
Сергей Анатольевич Вакаров
Мария Григорьевна Алексеева
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Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1. Амиды N-(2-аминопурин-6-ил)-6-аминокапроновой кислоты общей формулы 1(1),где (1a) R=Me, R'=H, X=O, Y=Z=F;(1b) R=H, R'=Me, X=O, Y=Z=F;(1c) R=Me, R'=H, X=CH, Y=Z=H;(1d) R=H, R'=Me, X=CH, Y=Z=H;(1e) R=Me, R'=H, X=CH, Y=Z=F;(1f) R=H, R'=Me, X=CH, Y=Z=F.2. Соединения формулы 1 по п. 1, обладающие противоопухолевой активностью.3. Способ получения амидов N-(2-аминопурин-6-ил)-6-аминокапроновой кислоты по п. 1 путем ацилирования соответствующих энантиомерно чистых хиральных гетероциклических аминов общей формулы,где X, Y, Z, R и R′ имеют вышеуказанные значения, хлорангидридом 6-фталимидокапроновой кислоты, удаления фталоильной защитной группы под действием гидразин гидрата, нуклеофильного замещения полученными соединениями атома хлора в 2-ацетамидо-6-хлорпурине и последующего щелочного гидролиза ацетильной группы в полученном продукте.1. Amides of N- (2-aminopurin-6-yl) -6-aminocaproic acid of the general formula 1 (1), where (1a) R = Me, R '= H, X = O, Y = Z = F; ( 1b) R = H, R '= Me, X = O, Y = Z = F; (1c) R = Me, R' = H, X = CH, Y = Z = H; (1d) R = H, R '= Me, X = CH, Y = Z = H; (1e) R = Me, R' = H, X = CH, Y = Z = F; (1f) R = H, R '= Me, X = CH, Y = Z = F.2. Compounds of formula 1 according to claim 1, having antitumor activity. 3. The method for producing N- (2-aminopurin-6-yl) -6-aminocaproic acid amides according to claim 1 by acylating the corresponding enantiomerically pure chiral heterocyclic amines of the general formula, wherein X, Y, Z, R and R ′ have the above meanings, with acid chloride 6-phthalimidocaproic acid, removal of the phthaloyl protective group by hydrazine hydrate, nucleophilic substitution of the chlorine atom compounds in 2-acetamido-6-chloropurine and subsequent alkaline hydrolysis of the acetyl group in the resulting product.

Claims (3)

1. Амиды N-(2-аминопурин-6-ил)-6-аминокапроновой кислоты общей формулы 11. Amides of N- (2-aminopurin-6-yl) -6-aminocaproic acid of the general formula 1
Figure 00000001
(1),
Figure 00000001
(one), где (1a) R=Me, R'=H, X=O, Y=Z=F;where (1a) R = Me, R '= H, X = O, Y = Z = F; (1b) R=H, R'=Me, X=O, Y=Z=F;(1b) R = H, R '= Me, X = O, Y = Z = F; (1c) R=Me, R'=H, X=CH2, Y=Z=H;(1c) R = Me, R '= H, X = CH 2 , Y = Z = H; (1d) R=H, R'=Me, X=CH2, Y=Z=H;(1d) R = H, R '= Me, X = CH 2 , Y = Z = H; (1e) R=Me, R'=H, X=CH2, Y=Z=F;(1e) R = Me, R '= H, X = CH 2 , Y = Z = F; (1f) R=H, R'=Me, X=CH2, Y=Z=F.(1f) R = H, R '= Me, X = CH 2 , Y = Z = F. 2. Соединения формулы 1 по п. 1, обладающие противоопухолевой активностью.2. The compounds of formula 1 according to claim 1, having antitumor activity. 3. Способ получения амидов N-(2-аминопурин-6-ил)-6-аминокапроновой кислоты по п. 1 путем ацилирования соответствующих энантиомерно чистых хиральных гетероциклических аминов общей формулы3. The method of producing amides of N- (2-aminopurin-6-yl) -6-aminocaproic acid according to claim 1 by acylation of the corresponding enantiomerically pure chiral heterocyclic amines of the general formula
Figure 00000002
,
Figure 00000002
, где X, Y, Z, R и R′ имеют вышеуказанные значения, хлорангидридом 6-фталимидокапроновой кислоты, удаления фталоильной защитной группы под действием гидразин гидрата, нуклеофильного замещения полученными соединениями атома хлора в 2-ацетамидо-6-хлорпурине и последующего щелочного гидролиза ацетильной группы в полученном продукте. where X, Y, Z, R and R ′ have the above meanings, 6-phthalimidocaproic acid chloride, removal of the phthaloyl protecting group by hydrazine hydrate, nucleophilic substitution of the resulting chlorine atom compounds in 2-acetamido-6-chloropurine, and subsequent alkaline hydrolysis of the acetyl group in the resulting product.
RU2015101582/04A 2015-01-21 2015-01-21 Amides of n-(2-aminopurin-6-yl)-6-aminocaproic acid, having anti-tumour activity and synthesis method thereof RU2599577C2 (en)

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