Новые методы модификации стероидов с помощью реакций кросс-сочетания тема диссертации и автореферата по ВАК РФ 02.00.03, кандидат химических наук Латышев, Геннадий Владимирович

• Латышев, Геннадий Владимирович
• кандидат химических наук
• 2006

Оглавление диссертации кандидат химических наук Латышев, Геннадий Владимирович

Список использованных в работе обозначений.

Введение.

Обзор литературы.

1. Реакция Сузуки-Мийауры: закономерности и современные варианты.

1.1. Каталитический цикл реакции Сузуки.

1 2 Закономерности реакции Сузуки

1.3. Катализаторы в реакции Сузуки

1.4. Никель - катализируемая реакция Сузуки.

2. Реакции кросс-сочетания в химии стероидов.

2.1. Реакция Сузуки.

2 2. Реакция Соногаширы.

2 3. Реакция Стилле.

2.4. Реакция Негиши

2.5. Реакция Хека.

Обсуждение результатов.

1. Синтез галогенстероидов.

1.1.4- и 6-бромпроизводные стероидов.

1.2. Синтез 3- и 17- иодстероидов.

2. Арилирование хлор- и бром- Д4-3-кетостероидов.

2.1. Арилирование хлормадинонацетата.

2.2. Арилирование 4-бромстероидов

2.3. Арилирование 6-бром-Д4 6-3-кетостероидов.

2 4. Синтез 6-арил-Д4-стероидов.

3. Алкинилирование 6-бромстероидов.

4. Арилирование 3- и 17- иодстероидов.

5. Бензилирование и алкилирование галогенстероидов.

6. Биологическая активность полученных соединений.

Экспериментальная часть.

1. Очистка растворителей.

2. Синтез исходных соединений.

2.1. Синтез 4-бром стероидов.

2 2. Синтез 6-замещенных стероидов

2 3 Синтез 3- и 17- галогенстероидов.

2 4. Синтез N-тозилиндол-З-илборной кислоты.

3. Кросс-сочетание 4- и 6-галогенстероидов с арилборными кислотами.

3.1. Арилирование 17а-ацетокси-6-хлор-прегна-4,6-диен-3,20-диона.

3.2. Арилирование 4-бромстероидов.

3.3. Арилирование 6-бром-андроста-4,6-диен-3,17-диона.

3 4. Арилирование 17а-ацетокси-6-бром-прегна-4,6-диен-3,20-диона.

3.5. Синтез 6-арил-Д4-стероидов.

4. Кросс-сочетание 6-бромстероидов с терминальными ацетиленами.

4.1. Алкинилирование 6-бром-3-метоксиандроста-3,5-диен-17-она.

4.2. Алкинилирование 6-бром-андроста-4,6-диен-3,17-диона.

5. Кросс-сочетание 3- и 17-иодстероидов с арилборными кислотами.

5.1. Арилирование 17-галогенстероидов.

5.2. Арилирование 17-гидрокси-3-иодандроста-3,5-диена.

6. Кросс-сочетание галогенстероидов с цинкорганическими соединениями.

6.1. Получение Zn-органических соединений.

6 2. Алкилирование 6-бромстероидов.

6 3. Бензилирование 3-иодстероидов.

6 4, Алкилирование 17-иодандроста-4,16-диен-3-она.

Выводы.

Введение диссертации (часть автореферата) на тему «Новые методы модификации стероидов с помощью реакций кросс-сочетания»

Разработка новых лекарственных препаратов путем модификация природных биологически активных веществ является одним из наиболее эффективных подходов к синтезу новых селективных терапевтических агентов. Среди многообразия доступных субстратов стероиды занимают особое положение, во многом связанное с их высокой активностью и участием в важнейших процессах, протекающих в организме. Общность структур основных стероидных гормонов и, в то же время, высокая зависимость их биологической активности от положения и природы заместителей, делают стероидные субстраты идеальными предшественниками для синтеза соединений, гарантированно обладающих биологической активностью.

В целом ряде клинических ситуаций избыточные (или даже нормальные) количества продуцируемых организмом стероидных гормонов играют значительную роль в патогенезе гормон-зависимых заболеваний. Поэтому подавление биосинтеза этих гормонов путем ингибирования соответствующих ферментов является одним из путей достижения прогресса в клинике таких распространенных заболеваний как рак молочной железы, яичников, простаты и некоторых других. За последние 10-15 лет были синтезированы различные производные стероидов, проявляющие ингибирующее действие по отношению к ароматазе и 5-а-редуктазе, ответственных за накопление эстрогенов и андрогенов в организме человека [1]. Для синтеза таких производных были широко использованы методы классической органической химии. Сравнительно недавно в химии стероидов начал использоваться новый, предоставляющий широкие синтетические возможности метод модификации стероидного скелета, основанный на реакциях кросс-сочетания [2]. Однако, круг используемых в таких реакциях стероидных субстратов был крайне ограничен. В первую очередь это связано с использованием в качестве субстратов трифлатов енолов соответствующих кетостероидов, что практически не позволяло вводить заместители в положения стероида, отличные от 3-его и 17-го. В связи с этим, разработка новых методов модификации стероидов, основанных на использовании реакций кросс-сочетания галогенстероидов, катализируемых комплексами переходных металлов, с целью синтеза соединений, обладающих потенциальной фармакологической активностью, является актуальной и практически важной задачей.

Целью настоящей работы является разработка новых каталитических способов синтеза арил, бензил и алкинилзамещенных стероидов на основе реакций кросс-сочетания галогенстероидов с бор- и цинкорганическими соединениями, а также с терминальными ацетиленами.

В результате проведенных исследований был разработан удобный метод синтеза ранее практически не известных 4- и 6-арилстероидов ряда андростана и прегнана с помощью Pd-катализируемой реакции Сузуки-Мийауры. В отличие от традиционных подходов к синтезу таких соединений, предложенный метод позволяет легко вводить функционально-замещенные арильные и гетарильные группы в стероиды.

Впервые показано, что коммерчески доступный неактивированный хлорстероид -хлормадинонацетат, имеющий атом хлора у sp2 атома углерода, может быть с успехом введен в реакцию Сузуки-Мийауры. Ключевым условием, позволяющим добиться высоких выходов арилстероидов является использование в качестве катализаторов комплексов палладия с бидентатными лигандами.

Впервые предложен простой и удобный способ синтеза 6-арил-3-кето-Д4-стероидов, содержащих арильную группу, связанную с зр3-гибридизованным атомом углерода, основанный на реакции Сузуки-Мийауры енолэфиров 6-бром-З-кетостероидов с арилборными кислотами. Данный метод позволяет избежать использования в реакциях кросс-сочетания малостабильных 6-бром-Д4-стероидов, имеющих атом брома в аллильном положении, а также является значительно более эффективным и универсальным, чем известные некаталитические методы синтеза подобных соединений.

Оптимизированы условия проведения реакции Сузуки-Мийауры 3- и 17-иодстероидов. Предложенный метод позволяет значительно увеличить выходы соответствующих арилированных стероидов. Найденные условия были использованы для синтеза широкого круга 3-арилстероидов.

Разработан эффективный метод синтеза 6-алкинилзамещенных производных андростана с помощью Pd-катализируемой реакции Соногаширы-Хагихары. Показано, что использование в качестве сокатализатора AgCl в присутствии пиперидина и воды позволяет значительно увеличить активность каталитической системы.

Изучена возможность использования реакции Негиши для введения бензильных и алкильных групп в стероиды. Разработанный протокол позволяет в исключительно мягких условиях получать 3-й 6-бензил- и алкилзамещенные стероиды с высокими выходами.

Литературный обзор состоит из двух частей. Первая часть посвящена реакции Сузуки-Мийауры. Особое внимание уделено современной (2000 - начало 2006 г) литературе, посвященной разработке новых высоко эффективных катализаторов реакции. Во второй части литературного обзора описаны известные случаи реаций кросс-сочетания стероидов.

Основное содержание работы изложено в публикациях [3-10]. Материалы диссертации доложены на международной конференции студентов и аспирантов по фундаментальным наукам "Ломоносов-2004" (Москва, 2004), на конференции "Фундаментальные науки - медицине" (Москва, 2004), на 3-м московском международном конгрессе "Биотехнология: состояние и перспективы развития" (Москва, 2005), на 21-й конференции по изопреноидам, (Польша, 2005).

Работа выполнена при финансовой поддержке Российского фонда фундаментальных исследований (грант № 04-03-32995) и Российской Академии Наук (программа Ю-ОХН).

Обзор литературы

Заключение диссертации по теме «Органическая химия», Латышев, Геннадий Владимирович

Выводы

1. Разработан эффективный метод синтеза широкого круга ранее неизвестных 6-(гет)арил-3-кето-Д46-стероидов ряда андростана и прегнана с помощью Pd-катализируемого арилирования арилборными кислотами (реакции Сузуки-Мийауры).

2. Показано, что использование бидентатных лигандов позволяет ввести в реакцию Сузуки-Мийауры хлормадинонацетат, содержащий связь Csp2-Cl.

3. Предложен оригинальный, простой и удобный способ синтеза 6-арил-З-кето-Д4-стероидов, содержащих арильную группу, связанную с зр3-гибридизованным атомом углерода, основанный на реакции Сузуки енолэфиров 6-бром-З-кетостероидов с арилборными кислотами.

4. Разработаны эффективные методы синтеза 3- и 4-арилзамещенных стероидов.

5. Разработан эффективный метод синтеза 6-алкинилзамещенных производных андростана с помощью Pd-катализируемой реакции Соногаширы-Хагихары. Впервые показано, что использование в качестве сокатализатора AgCl в присутствии пиперидина и воды позволяет значительно увеличить активность каталитической системы.

6. Разработана методика, позволяющая в мягких условиях получать разнообразные бензилзамещенные стероиды с помощью Pd-катализируемой реакции с цинкорганическими соединениями (реакции Негиши).

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