Buchwald-Hartwig amination of the chloro substituted benzobicyclo[3.2.1]octadiene skeleton using primary benzylic amines

Ratković, Ana; Kelava, Vanja; Marinić, Željko; Škorić, Irena

doi:10.1016/j.molstruc.2018.11.057

Cited by 5 publications

(4 citation statements)

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“…Compound endo - 1 was obtained in one photochemical step according to the described method from the previously prepared o -vinylphenyl substituted butadienes [ 31 ]. The Buchwald−Hartwig amination successfully gave amino substituted benzobicyclo[3.2.1]octadienes endo - 2 – 18 ( Scheme 1 ) at 21–88% yields [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

Benzobicyclo[3.2.1]octene Derivatives as a New Class of Cholinesterase Inhibitors

et al. 2020

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A library of amine, oxime, ether, epoxy and acyl derivatives of the benzobicyclo[3.2.1]octene were synthesized and evaluated as inhibitors of both human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The majority of the tested compounds exhibited higher selectivity for BChE. Structural adjustment for AChE seems to have been achieved by acylation, and the furan ring opening of furo-benzobicyclo[3.2.1]octadiene results for compound 51 with the highest AChE affinity (IC50 = 8.3 µM). Interestingly, its analogue, an oxime ether with a benzobicyclo[3.2.1]-skeleton, compound 32 was one of the most potent BChE inhibitors in this study (IC50 = 31 µM), but not as potent as endo-43, an ether derivative of the benzobicyclo[3.2.1]octene with an additional phenyl substituent (IC50 = 17 µM). Therefore, we identified several cholinesterase inhibitors with a potential for further development as potential drugs for the treatment of neurodegenerative diseases.

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Section: Resultsmentioning

confidence: 99%

Benzobicyclo[3.2.1]octene Derivatives as a New Class of Cholinesterase Inhibitors

et al. 2020

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“…13 (E)-2-(4-chlorostyryl)thiophene (trans-1): 370 mg (isolated, 44%), white powder, m.p. 98-100 • C; R f (PE) = 0.85; UV (ACN) λ max /nm (ε/dm 3 mol −1 cm −1 ) 327 (35,185). 1 H NMR (CDCl 3 , 600 MHz) δ/ppm: 7.41-7.36 (m, 2H), 7.33-7.28 (m, 2H), 7.23-7.17 (m, 2H), 7.07 (dt, J = 3.4, 0.8 Hz, 1H), 7.01 (dd, J = 5.1, 3.6 Hz, 1H), 6.87 (d, J = 16.1 Hz, 1H).…”

Section: -(4-chlorostyryl)thiophene (1) [34]mentioning

confidence: 99%

“…A closer look into the nature and position of the substituent on the isolated yield (Scheme 1) reveals that the m-fluoro (cis-3) and thienyl (cis-8) derivatives give the best yields in the case of cis-configuration, as well as of trans-amines. Based on our previous results [35], where the ortho substitution on the arylamines gave the lowest yields, we decided to exclude this kind of starting amine at this point of the investigation. However, the ortho substitutions usually result in compounds with some unique properties; therefore, they will be considered and studied in separate research.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Photochemistry, Computational Study and Potential Application of New Styryl-Thiophene and Naphtho-Thiophene Benzylamines

Mlakić

Odak

Faraho

et al. 2022

IJMS

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In this research, the synthesis, photochemistry, and computational study of new cis- and trans-isomers of amino-thienostilbenes is performed to test the efficiency of their production and acid resistance, and to investigate their electronic structure, photoreactivity, photophysical characteristics, and potential biological activity. The electronic structure and conformations of synthesized thienostilbene amines and their photocyclization products are examined computationally, along with molecular modeling of amines possessing two thiophene rings that showed inhibitory potential toward cholinesterases. New amino-styryl thiophenes, with favorable photophysical properties and proven acid resistance, represent model compounds for their water-soluble ammonium salts as potential styryl optical dyes. The comparison with organic dyes possessing a trans-aminostilbene subunit as the scaffold shows that the newly synthesized trans-aminostilbenes have very similar absorbance wavelengths. Furthermore, their functionalized cis-isomers and photocyclization products are good candidates for cholinesterase inhibitors because of the structural similarity of the molecular skeleton to some already proven bioactive derivatives.

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“…Mjerenja eksperimentalnih fizikalno-kemijskih i ADME svojstava dobivenih fotoprodukata, njihove biološke aktivnosti i inhibicijske aktivnosti prema kolinesterazama također su vrlo obećavajuća. Obećavajući rezultati ispitivanja biološke aktivnosti potiču na nastavak funkcionalizacije 49 u smjeru priprave novih amino-, oksimskih, eterskih, esterskih te hidroksilnih i acilnih derivata benzobiciklo[3.2.1]-skeleta (slika 5. ).…”

Section: Znanstvena Istraživanja Na Zavodu Za Organsku Kemijuunclassified

Znanstveno-istraživačka djelatnost Zavoda za organsku kemiju u razdoblju 2009. – 2019.

et al. 2019

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Od osnutka Zavoda za organsku kemiju Fakulteta kemijskog inženjerstva i tehnologije Sveučilišta u Zagrebu, koji je 1922. god. osnovao prof. dr. Ivan Marek, te kasnije preko djelovanja nobelovca Vladimira Preloga i brojnih uspješnih generacija organskih kemičara, vidljiv je utjecaj ne samo na znanstvenu djelatnost Zavoda nego i na cjelokupnu hrvatsku kemijsku zajednicu, osobito u području organske sintetske i medicinske kemije. Preparativnu organsku kemiju profesor Prelog držao je nužnom odrednicom studija, koja je zahvaljujući njegovu djelovanju u Zavodu (1935. – 1941.) ostala glavna okosnica znanstveno-istraživačkog rada. Od samog osnivanja u laboratorijima Zavoda odvijaju se istraživanja iz područja sintetske organske i medicinske kemije i fotokemije, stječu se znanstveni stupnjevi i obrazuju brojni organski kemičari, među kojima su danas mnogi priznati znanstvenici u Hrvatskoj i svijetu.

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Buchwald-Hartwig amination of the chloro substituted benzobicyclo[3.2.1]octadiene skeleton using primary benzylic amines

Cited by 5 publications

References 37 publications

Benzobicyclo[3.2.1]octene Derivatives as a New Class of Cholinesterase Inhibitors

Benzobicyclo[3.2.1]octene Derivatives as a New Class of Cholinesterase Inhibitors

Synthesis, Photochemistry, Computational Study and Potential Application of New Styryl-Thiophene and Naphtho-Thiophene Benzylamines

Znanstveno-istraživačka djelatnost Zavoda za organsku kemiju u razdoblju 2009. – 2019.

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