CS268890B1 - Halogen derivatives of 3-phenyl-1-oxo-indene-2-yl acetic acid and method of their preparation - Google Patents
Halogen derivatives of 3-phenyl-1-oxo-indene-2-yl acetic acid and method of their preparation Download PDFInfo
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- CS268890B1 CS268890B1 CS887624A CS762488A CS268890B1 CS 268890 B1 CS268890 B1 CS 268890B1 CS 887624 A CS887624 A CS 887624A CS 762488 A CS762488 A CS 762488A CS 268890 B1 CS268890 B1 CS 268890B1
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Description
CS 268890 Ql 1
Vynález se týkáobecného vzorce I nových halogender ivátú kyše 1iny 3-feny1-i-oxo-inden-2-y1 octové
1 2 12ve kterém Rx značí vodík a R chlor nebo R i R brom. 1 2 Látky obecného vzorce I o výše uvedeném významu R a R jsou cennými meziproduktypro přípravu látek se zajímavými biologickými účinky, především tetracyklických deri-vátu benzo(c)fluorenu. Deriváty benzo(c)fluorenu vykazují významnou protinádorovou,interferonogenní a antibakteriálni aktivitu (Křepelka a pol. Collect. Czech. chem.Commun. 47, 1258 (1982), 47, 1857 (1982), Vančurová a »pol. Collect. Czech. Chem.Commun. £7, 1867 (1982), AO č. 212 669, USA patent č. 4,661.297, Šmejkal a spol. Actavirol. 29, li (I984))a látky obecného vzorce I jsou významnými prekureory při jejichsyntéze. 1 2 Látky obecného vzorce I o výše uvedeném významu R a R se podle vynálezu připravíz odpovídajících halogenovaných difenylitakonových kyselin obecného vzorce n
1 2 12 ve kterém R značí vodík a R chlor nebo R i R brom, čs. autorské osvědčení č. 268889 cyklizací v prostředí minerální kyseliny, výhodně kyseliny sírové, při O °C.
Podrobnější údaje o přípravě látek obecného vzorce I o výše uvedeném významu R1 2 2 a R vyplynou z následujícího příkladu provedení, který rozsah vynálezu nijak neomezuje,příklad
Kyselina 3-(3-bromfenyl)-5-brom-l-oxo-inden-2-yl octové
Za chlazení ledem bylo do tříhrdlé baňky opatřené zpětným chladičem a míchadlemvneseno 14 g (0,032 mol) kyseliny 3,3'-dibrom-difenylitakonové do 22,4 ml (0,41 mol)koncentrované kyseliny sírové. Černý roztok byl za chlazení míchán 3 hodiny. Poté bylareakční směs vlita do kádinky s ledem a míchána až do jeho rozpuštění. Vzniklá žlutásraženina byla odsáta a promyta vodou. Nato byla sraženina převedena do Erlenmeyerovybaňky a přidáno 130 ml vody a 3 g (0,075 mol) hydroxidu sodného a směs zahřívána dovytvoření homogenního roztoku, který byl za horka zfiltrován a okyselen koncentrovanoukyselinou chlorovodíkovou na pH = 3. Vyloučená žlutá sraženina byla odsáta, a sušena vol-ně na vzduchu. Rekrystalizací z ethanolu byla získána látka o teplotě tání 107 až 110 °CBylo získáno 11,8 g (88,6 %) produktu).
Analogicky byla připravena kyselina 3-(3-chlorfenyl)-l-oxo-inden-2-yl octová, T. t = 102 až 104 °C.
CS 268890 Q1
The present invention relates to the general formula I of the novel halogenated tartaric acid 3-phenyl-i-oxo-inden-2-yl acetic acid.
Wherein R x is hydrogen and R is chlorine or R 1 is bromo. The compounds of formula I as defined above for R and R are valuable intermediates for the preparation of compounds with interesting biological effects, in particular tetracyclic benzo (c) fluorene derivatives. Benzo (c) fluorene derivatives show significant antitumor, interferonogenic and antibacterial activity (Quail and Collect. Czech. Chem. Commun. 47, 1258 (1982), 47, 1857 (1982), Vančurová and Collect. Czech.). Chem. Commun., 7, 1867 (1982), AO No. 212,669, U.S. Patent No. 4,661,297, Smejkal et al., Actavirol. 29, 11 (1984), and compounds of Formula I are important precursors in their synthesis. The compounds of formula I of the above-mentioned R and R are prepared according to the invention by the corresponding halogenated diphenylitaconic acids of the formula n
Wherein R is hydrogen and R is chlorine or R 1 is bromo, MS. Author's Certificate No. 268889 cyclized in a mineral acid environment, preferably sulfuric acid, at 0 ° C.
More details on the preparation of compounds of formula I of the above-mentioned definition of R 2 2 and R 2 will result from the following non-limiting example.
3- (3-Bromophenyl) -5-bromo-1-oxo-inden-2-yl acetic acid
Under ice-cooling, 14 g (0.032 mol) of 3,3 ' -dibromo-diphenylitaconic acid were charged into 22.4 ml (0.41 mol) of concentrated sulfuric acid in a three-necked flask equipped with a reflux condenser and stirred. The black solution was stirred with cooling for 3 hours. Then the reaction mixture was poured into a beaker of ice and stirred until dissolved. The resulting yellow precipitate was filtered off with suction and washed with water. Subsequently, the precipitate was transferred to an Erlenmeyer flask and 130 ml of water and 3 g (0.075 mol) of sodium hydroxide were added, and the mixture was heated to form a homogeneous solution which was hot filtered and acidified with concentrated hydrochloric acid to pH = 3. in the air. Recrystallization from ethanol gave the product, m.p. 107-110 ° C, 11.8 g (88.6%) of product).
3- (3-Chlorophenyl) -1-oxo-inden-2-yl acetic acid was prepared analogously, mp = 102-104 ° C.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS887624A CS268890B1 (en) | 1988-11-21 | 1988-11-21 | Halogen derivatives of 3-phenyl-1-oxo-indene-2-yl acetic acid and method of their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS887624A CS268890B1 (en) | 1988-11-21 | 1988-11-21 | Halogen derivatives of 3-phenyl-1-oxo-indene-2-yl acetic acid and method of their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS762488A1 CS762488A1 (en) | 1989-08-14 |
| CS268890B1 true CS268890B1 (en) | 1990-04-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS887624A CS268890B1 (en) | 1988-11-21 | 1988-11-21 | Halogen derivatives of 3-phenyl-1-oxo-indene-2-yl acetic acid and method of their preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS268890B1 (en) |
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1988
- 1988-11-21 CS CS887624A patent/CS268890B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS762488A1 (en) | 1989-08-14 |
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