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Marek Lukáš - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis o kinase inhibitors containing 3-[amino(aryl)methylidene]-1,3-dihydro-2H-indol-2-one skeleton
    'Univerzita Pardubice', 2019
    Co-Authors: Marek Lukáš
    Abstract:

    V teoretické části této kvalifikační práce je diskutována významná role 3-[amino(aryl)methyliden]-1,3-dihydro-2H-indol-2-onů v moderní terapii nádorových onemocnění. Součástí je taktéž rešerše veškerých, celkem 12-ti v literatuře dosud popsaných syntetických metod, poskytujících jako produkty právě tyto látky, z nichž některé byly publikovány teprve nedávno. Experimentální část práce se zabývá novou a efektivní metodou pro syntézu látek s 3-[amino(aryl)methyliden]-1,3-dihydro-2H-indol-2-onovým. V rámci zkoumání reakce 3-bromo-1,3-dihydro-2H-indol-2-onů s thiobenzamidy mechanismem Eschenmoserovy reakce, resp. jejího průběhu v závislosti na substituci zmíněných sloučenin a dalších faktorech, bylo připraveno celkem 14 látek obsahujících 3-[amino(aryl)methyliden]oxindolový skelet. Ze syntetizovaných látek již bylo 8 v literatuře popsáno, jedná se o látky mající stanovenou inhibiční aktivitu na tyrosin-kinázových VEGF receptorech. Pro tyto látky byla doplněna v literatuře chybějící charakterizace (NMR, HRMS). Zbývajících 6 látek jsou sloučeniny zcela nové - ty byly kompletně charakterizovány pomocí bodu tání, 1H a 13C NMR, HRMS a elementární analýzy.Importance of compounds containing 3-[amino(aryl)methylidene]-1,3-dihydro-2H-indol-2-one structure moiety in modern cancer treatment is discussed in theoretical section of this diploma thesis together with up to date known synthetic methods. Overall 12 different known synthetic pathways giving mentioned compounds are also discussed; some of them were published very recently. A new, efficient and high-yielding synthetic method giving compounds containing 3-[amino(aryl)methylidene]-1,3-dihydro-2H-indol-2-one moiety is described in this diploma thesis. In summary, 14 compounds were prepared during exploration of very rare example of thiophile-free Eschenmoser Reaction using various 3-bromo-1,3-dihydro-2H-indol-2-ones and thiobenzamides as starting materials. Eight of them were previously described in literature as potent tyrosine-kinase VEGF receptor inhibitors. For these mentioned compounds, missing characterization such as NMR spectra or HRMS were completed. The rest represent original compounds unknown in literature up to date, for which complete characterization by melting point, 1H and 13C NMR, HRMS spectra and elemental analysis is included.Fakulta chemicko-technologickáDiplomant přednesl cca 15 min. přednášku na téma své diplomové práce s názvem "Syntéza inhibitorů kináz s 3-[amino(aryl)methyliden]-1,3-dihydro-2H-indol-2-onovým skeletem". Po přečtení posudku školitele a oponentky se diiplomant vyjádřil k dotazům oponentského posudku. K obhajobě práce byly dále vzneseny následující dotazy: prof. Ing. Miroslav Ludwig, CSc. Zkoušel jste ze začátku i jiná rozpouštědla než jste přešel k DMF? prof. RNDr. Milan Potáček, CSc. Testoval jste vámi připravené látky? doc. Ing. Petr Šimůnek, Ph.D. Jak si vysvětlujete brzděnou rotaci?Dokončená práce s úspěšnou obhajobo

Kolman Lukáš - One of the best experts on this subject based on the ideXlab platform.

  • 3-[Amino(aryl)methylidene]-1,3-dihydro-2H-indol-2-ones with tertiary amino group
    'Univerzita Pardubice', 2020
    Co-Authors: Kolman Lukáš
    Abstract:

    Předložená práce se zabývá syntézou 3-[amino(aryl)methyliden]indol-2-onů s terciární aminoskupinou s využitím Eschenmoserovy reakce. Bylo připraveno a charakterizováno 7 nových dosud nepopsaných látek, nesoucích substituenty na obou aromatických jádrech a methylové skupiny na dusíku aminoskupiny. Výtěžky těchto látek jsou v rozmezí od 19 do 83 % a jsou ovlivněny jak substitucí, tak i podmínkami separace. Klíčová je i přítomnost thiofilu (trimethyl-fosfitu). Dále byl připraven a charakterizován i jeden derivát nesoucí na dusíku dvě ethylskupiny a to ve výtěžku 57 %. Byl učiněn i pokus o přípravu N-methyl-N-fenyl derivátu 3-[amino(aryl)methyliden]indol-2-onu, který však díky nízké rozpustnosti nebylo možné řádně vyčistit a charakterizovat.The present work deals with the synthesis of 3-[amino(aryl)methylidene]indol-2-ones with a tertiary aminogroup using the Eschenmoser Reaction. Prepared and characterized were 7 new hitherto undescribed substances bearing substituents on both aromatic rings and methyl substituents on the nitrogen of the aminogroup. Yields of these substances are in the range from 19 to 83% and are affected by both substitution and separation conditions. The presence of thiophile (trimethyl-phosphite) is also crucial. Furthermore, one derivative bearing two ethyl groups on nitrogen was prepared and characterized in a yield of 57%. An attempt was also made to prepare the N-methyl-N-phenyl derivative of 3-[amino(aryl)methylidene]indol-2-one, which could not be properly purified and characterized due to its low solubility.Fakulta chemicko-technologickáStudent prezentoval svoji bakalářskou práci a vyjádřil se k připomínkám.Dokončená práce s úspěšnou obhajobo

V. G. Granik - One of the best experts on this subject based on the ideXlab platform.

Kazumi Shiosaki - One of the best experts on this subject based on the ideXlab platform.

  • 3.7 – The Eschenmoser Coupling Reaction
    Comprehensive Organic Synthesis, 1991
    Co-Authors: Kazumi Shiosaki
    Abstract:

    The Eschenmoser coupling Reaction represents a versatile and efficient method to prepare vinylogous amides and urethanes by alkylation of a secondary or tertiary thioamide with an appropriate electrophilic component followed by elimination of sulfur (equation 1). This coupling, which in essence condenses an enolizable carbon with an amide carbonyl, can be formally considered a variant of the Claisen condensation. An extension of this process through alkylation of thiocarboxylic acids leads to direct synthesis of 1,3-dicarbonyl compounds (equation 2). Vinylogous amides and carbamates along with their hydrolysis products, the 1,3-dicarbonyl compounds, are important synthetic intermediates; their value is attested by the numerous methods available for their synthesis.1,2 The Eschenmoser Reaction provides an alternative approach to prepare these compounds that offers several distinct advantages. The unambiguous formation of a particular vinylogous amide or carbamate or a substituted 1,3-dicarbonyl compound can be achieved. Since the Reaction conditions are sufficiently mild, incorporation of various functional groups and preservation of base-sensitive stereocenters are possible. The reacting centers also are relatively insensitive to the steric environment. In addition, the range of applications now available to the Reaction has been broadened significantly through modifications and extensions on the original studies.

  • 3 7 the Eschenmoser coupling Reaction
    Reference Module in Chemistry Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis, 1991
    Co-Authors: Kazumi Shiosaki
    Abstract:

    The Eschenmoser coupling Reaction represents a versatile and efficient method to prepare vinylogous amides and urethanes by alkylation of a secondary or tertiary thioamide with an appropriate electrophilic component followed by elimination of sulfur (equation 1). This coupling, which in essence condenses an enolizable carbon with an amide carbonyl, can be formally considered a variant of the Claisen condensation. An extension of this process through alkylation of thiocarboxylic acids leads to direct synthesis of 1,3-dicarbonyl compounds (equation 2). Vinylogous amides and carbamates along with their hydrolysis products, the 1,3-dicarbonyl compounds, are important synthetic intermediates; their value is attested by the numerous methods available for their synthesis.1,2 The Eschenmoser Reaction provides an alternative approach to prepare these compounds that offers several distinct advantages. The unambiguous formation of a particular vinylogous amide or carbamate or a substituted 1,3-dicarbonyl compound can be achieved. Since the Reaction conditions are sufficiently mild, incorporation of various functional groups and preservation of base-sensitive stereocenters are possible. The reacting centers also are relatively insensitive to the steric environment. In addition, the range of applications now available to the Reaction has been broadened significantly through modifications and extensions on the original studies.

T. I. Mukhanova - One of the best experts on this subject based on the ideXlab platform.