Синтез и модификация морфинановых и родственных систем: металлоорганический подход
Диссертация
По мере накопления экспериментальных данных относительно лиганд-рецепторного взаимодействия, свойств и механизмов фармакологического действия уже известных лекарственных средств, по мере развития на этой основе соответствующих теоретических воззрений поиск новых физиологически активных соединений среди представителей данных классов начал носить более целенаправленный характер. Цель этих… Читать ещё >
Содержание
- Список сокращений
- ГЛАВА 1. Морфинановые и родственные системы (литературный обзор)
- 1. 1. Опиоидные рецепторы и опиоидные лиганды
- 1. 2. Морфинановые и бензоморфановые алкалоиды: основные методы синтеза и направления модификации
- 1. 2. 1. Бензоморфаны
- 1. 2. 1. 1. Синтез бензоморфанов циклизацией по Греве
- 1. 2. 1. 2. Модификации синтеза Греве и другие методы
- 1. 2. 1. 3. Расширение и сужение кольца С в 6,7-бензоморфанах
- 1. 2. 1. 4. Фармакологическая активность 6,7-бензоморфанов
- 1. 2. 2. Морфинаны
- 1. 2. 2. 1. Полный синтез морфинанов циклизацией по Греве
- 1. 2. 2. 2. Полный синтез морфинанов другими методами
- 1. 2. 2. 3. Синтез морфинанов модификацией природных алкалоидов
- 1. 2. 2. 4. Фармакологическая активность морфинанов
- 1. 2. 3. 4,5 а-Эпоксиморфинаны
- 1. 2. 3. 1. Полный синтез 4,5"-эпоксиморфинанов
- 1. 2. 3. 2. Строение 4,5<2-эпоксиморфинанов
- 1. 2. 3. 3. Основные источники 4,5û-î--эпоксиморфинанов
- 1. 2. 3. 4. Модификация природных 4,5ск-эпоксиморфинанов
- 1. 2. 4. Синтезы на основе тебаина
- 1. 2. 4. 1. Окисление тебаина
- 1. 2. 4. 2. Реакции Дильса-Альдера на основе тебаина
- 1. 2. 4. 3. Тевинолы и орвинолы
- 1. 2. 1. Бензоморфаны
- 2. 1. Синтетические возможности, открывающиеся при комплексовании переходных металлов с лигандом, и место Сг в этом подходе
- 2. 2. Возможности, предоставляемые-аренхромтрикарбо-нильными комплексами в синтезе
- 2. 3. Свойства и получение-аренхромтрикарбонильных комплексов
- 2. 3. 1. Физико-химические свойства
- 2. 3. 2. Удаление Сг (СО)3-группы
- 2. 3. 3. Получение-аренхромтрикарбонильных комплексов
- 2. 4. Металлирование-аренхромтрикарбонильных комплексов
- 2. 4. 1. Направления и селективность металлирования
- 2. 4. 2. Нуклеофильная атака на ароматический лиганд в т^-аренхромтрикарбонильных комплексах
- 2. 4. 3. Деароматизация аренового лиганда в-аренхромтрикарбонильных комплексах
- 2. 4. 4. Электрофильная атака на ароматический лиганд в-аренхромтрикарбонильных комплексах
- 2. 4. 5. Депротонирование ароматического кольца в-аренхромтрикарбонильных комплексах
- 2. 4. 6. Альтернативные способы получения металлированных в кольцо-аренхромтрикарбонильных комплексов
- 2. 4. 7. Полилитирование 776-аренхромтрикарбонильныхкомплексов
- 2. 5. Реакции боковой цепи в-аренхромтрикарбонильных комплексах
- 2. 5. 1. Стабилизация бензильных карбанионов, карбокатионов и радикалов хромтрикарбонильной группой
- 2. 5. 2. Бензильные карбанионы, стабилизированные хромтрикарбонильной группой: получение и реакционная способность
- 2. 5. 3. Нуклеофильное присоединение к хромтрикарбонильным комплексам я-оксоаренов
- 2. 6. Стереохимические аспекты химии-аренхромтрикарбо-нильных комплексов
- 2. 6. 1. Энантиоселективное депротонирование-аренхромтрикарбонильных комплексов
- 2. 6. 2. Диастереоселективное депротонирование-аренхромтрикарбонильных комплексов
- 2. 7. ^-Аренхромтрикарбонильные производные металлов, отличных от лития
- 2. 8. Комплексование Сг (СО)3-группы с энантиомерно чистыми аренами
- 2. 9. Реакции кросс-сочетания с участием-аренхромтрикарбонильных комплексов
- 2. 10. Использование-аренхромтрикарбонильных комплексов в синтезе природных соединений
- 3. 1. Общая стратегия
- 3. 1. 1. СН-Кислотность (76-алкиларен)хромтрикарбонильных комплексов
- 3. 2. Селективное бензильное металлирование амидом натрия и реакция с ВгСН2СООЫа. Формирование каркаса 6,7-бензоморфана
- 3. 3. Бензильная функционализация (76-алкиларен)хромтрикарбонильных комплексов через металлирование амидами лития
- 3. 3. 1. Синтетические проблемы селективного бензильного депротонирования
- 3. 3. 2. Селективное металлирование амидами лития в бензильное положение. «-Силилирование
- 3. 3. 3. Карбоксилирование бензильных литиевых производных
- 3. 3. 4. 1,2-Присоединение бензильных литиевых призводных к карбонильным соединениям
- 3. 3. 5. Реакции бензильных литиевых призводных с алкилгалогенидами
- 3. 3. 6. Реакции переметаллирования бензильных литиевых произ -водных ('76-алкиларен)хромтрикарбонильных комплексов
- 3. 3. 6. 1. Реакции бензильных цинковых производных
- 3. 3. 6. 2. Реакционная способность [^-бензилмедь^хромтри-карбонильного комплекса
- 3. 3. 6. 3. Бензильные палладийорганические производные
- 4. 1. ТУ-Арильные производные морфинанов
- 4. 2. Рё-Катализируемая модификация аллильных фрагментов кольца С в морфинанах
- 4. 2. 1. Рё-Катализируемое аминирование бАхлор-б-дезоксикодеина
- 4. 2. 2. Рс1-Катализируемое алкенилирование кодеина и последующие реакции
- 5. /?, 6/?, 7/?, 14^,)-3−1идрокси-6-метокси-17-циклопро11илметил-4,5эпокси-6,14-этаноморфинан-7-ил]-3,3-Диметилбутан-2-ола обсуждение результатов)
- 5. 1. Описание проблемы
- 5. 2. Получение субстанции
- 5. 3. Свойства лекарственной формы
- 5. 3. 1. Доклиническая фармакология и токсикология
- 5. 3. 2. Эффективность по данным клинических испытаний
- 5. 4. Значение разработки
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