Antiestrogenic Activities of 3,8-Dihydroxy-6,11-dihydrobenzo[a]carbazoles with Sulfur-Containing Side Chains

Synthesis, cytostatic evaluation and structure activity relationships of novel bis-indolylmethanes and their corresponding tetrahydroindolocarbazoles

“…Its 1 H-NMR spectrum showed singlet signal at δ = 5.91 ppm for 2 protons (2CH), and 2 triplet signals every one for 4 protons (2CH 2 ) at δ = 2.03 ppm and 2.27 ppm, also the four NH indole protons appeared at 9.94 ppm as a broad signal. These data proved the similarity M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 6 European Journal of Medicinal Chemistry of the structure which confirmed additionally by its 13 C-NMR spectrum.…”

“…In brief, glacial acetic acid without solvent was used to catalyze the reaction of indoles (two equivalent moles) and aryl or heteroaryl aldehydes (one equivalent mole). With our new method via glacial acetic acid as a solvent the corresponding BIMs were formed in a high yields (86-98 %) and after a few hours (4)(5)(6) hours of stirring at room temperature. Some BIMs (1 a , b , c , d , e , k,n ) are known [39][40][41][42][43][44][45], their identities were proven by means of MS, NMR, IR spectra, and the other BIMs, (1 f,g,h,i,j,l ), are novel and could not be found in the literature.…”

“…The electrophilic substitution reactions of indoles with aromatic aldehydes afford corresponding BIMs. Several catalysts such as protic acids [3][4][5][6], Lewis acids [7][8][9][10], ionic liquids [11], and others are used to promote these reactions. The 3-position of indole is the preferred site for the electrophilic substitution reactions.…”

2,5-Diphenylfuran-based pure antiestrogens with selectivity for the estrogen receptor α

“…The highest binding affinity was found for the ethyl derivative 12b with an RBA of 23 which exceeded the RBA for ER␤ by a factor of 4 (Table 1). In previous studies we have shown, that the introduction of side chains with an appropriate functional group into non-steroidal ligands of the ER leads to potent estrogen antagonists devoid of any agonist activity [17,20,21]. Three different side chains were used in this study: The 6-pyrrolidinohexyl substituent (13a,b) which is also present in the 2-phenylindole derivative ZK 119,010 [22], the 10-(pentylsulfonyl)decyl group applied for the synthesis of the indole-based antiestrogen ZK 164,015 [17], and the 6-[Nmethyl-N-(3-pentylsulfanylpropyl)amino]hexyl side chain which we recently investigated.…”

Synthesis of Novel Indolo‐Spirocyclic Compounds

“…The reaction solution became pink and the color turned to dark red by leaving it stirring under reflux for about 1 h. Upon the reaction completion, as monitored by TLC (5% MeOH/CH 2 Cl 2 ), the reaction was worked up by adding 50 mL of water, neutralized by NH 4 OH, extracted with 100 mL ethyl acetate, for two times washed with water and brine, dried over anhydrous Na 2 SO 4 , filtered, and concentrated in vacuum. The crude reaction mixture was purified via column chromatography on silica gel eluted with (7% MeOH/CH 2 Cl 2 ) to afford compound 4, C 32 A 2.5 Mmol (0.25 g) of cyclohexanone and 2 mmol (0.234 g) of indole were added to a flask that contained 50 mL MeOH under stirring and heating until it completely dissolved. When the reaction solution became clear, a few drops of conc.…”