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XVI INTERNATIONAL SYMPOSIUM ,,ADVANCES IN THE CHBMISTRY OF HETEROORGANIC

CoMPoUNDs,, ORGANIZBD BY

centre of Molecular and Macromolecular studies Polish Academy of Science

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Section of Heteroorganic Chemistry

Polish Chemical Society

ŁoDZ November 15,2013

1

6th

International Symposium

,rAdvances in the Chemistry of Heteroorganic Compound

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is dedicated to

professor

piotr kiełbasiński on the occasion of his 65th birthday

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XVI International Symposium

,oAdvances in the Chemistry of Heteroorganic Compoundso'

ŁódźrNovember 15r20l3

9:15

-

9:30

9:30 - 10:15

oPENING SESSION I - Chairman Marian Mikołajczyk w-1 Janusz Rachoń (GdańsĘ Poland)

Dithiophosphoric acid and its selenium analogues in the synthesis of sulfur and selenium compounds.

10:15 11

:00

-

11:00

-

11

11:30 -

W_2

Hans-Urlich Reissig (Berlin, Germany)

Synthesis of heterocycles with alkoxyallenes

COFFEE BREAK

:30

l2:l5

SESSION II - Chariman Henryk Krawczyk w_3 Toshiaki Murai (Gifu, Japan) Optically active phosphoroselenoic acid derivatives bearing a l,I'-bi-2-naphthyl group as new chiral molecular tools

12z15 -

13:00

W-4

Christian V. Stevens (Ghent, Belgium) Exploiting continuous flow opportunities for scale-up

13:00 - 14:00

LUNCH

14:00 - 15:00

POSTER SESSION SESSION III - Chairman Grzegorz Mlostoń W-5 Christian Miiller (Berlino Germany)

15:00 - 15:45

Recent developments in the chemistry of lowcoordinate phosphorus heterocycles 15:45 -

16:30

16:30 - 16z45

W-6

CLoSING

Valerij A. Nikolaev (St. Petersbufgo Russia)

Fluorinated diazodiketones - unexplored area in the chemistry of aliphati c diazo compounds

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P_035 STRUCTURE AND NMR PRoPERTlEs oF PoTENTIAL ANT!_CANCER 6-AMlNo-2_THloURAclL DERlVAT|VEs G

' Adam Mickiewicz IJniversity in Poznań, Faculty of Chemistry, Umultowska 89 b,67-674 poznań ' Adam Mickiewicz lJniversity in Poznań, NanoBioMedical Centre, tJmultowska 85, 67-614 poznań

RecentlY several derivatives of 6-aiiiino-2-thiouracil (ATU)have been obtained and many of them have revealed high activity against different cancer cells t1-3]. other compounds of this ctass are Promising antifungal, anti-inflammatory and anesthetic agents. t4-5].

We rePort a PreParation of novel 6-amino-2-thiouracil derivatives, prepared by the reaction of 6_ amino-2-thiouracil with isomeric aromatic aldehydes, i.e. o-, ffi- and p- hydroxy- and o_, m_ and p_ ch!oro-benzaldehYdes. The prepared compounds have been characterized by lR and NMR

spectroscopy as well as mass spectrometry. The PreParation of ATU derivatives 1a-6a [hydroxyphenylo- and chlorophenylo-bis(6_amino-1,2 tetrahYdro-2-thio-4-oxo-pyrimidin-S-yl)-methanes] is depicted on Scheme 1.

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raŻYna Bartkowiak1'2*, Katarzyna Gawron', Łukasz popenda2 and Grzegorz Schroederl

I

H

O1_6

oOH 4 oCl 2 nr,OH 5 nrCl 3 pOH 6 pCl 1

,3,4_

---+

Scheme

products obtained:

la

- 6a

1

Mass sPectral data from electrospray ionization (ESl) and matrix-assisted laser desorption/ionization (MALDI) mass sPectra confirmed the exact mass of synthesized motecules and 13c 'H NMR and spectra authenticated their chemical structure. The exPeriments Peńormed proved that the amino group of ATU is not active in the applied reaction

conditions (heating of the substrates in DMF solution)and the formation of Schiff bases is not favored, since mainlY compounds of 1a-6a type, in which C5-hydrogen atom in ATU is substituted, are formed. References: [1] N, R Mohamed, M. T. Et-Saidi, Y.M.Ati, M. H Elnagdi, "Uti!ity of 6-amino-2_tio-uracil as a precursor for the sYnthesis of bioactive pyrimidine derivatives", Bioorganic & Medicinal Chemistry, L5,6227, (2oO7| [2] . Hala El-Nassan; Synthesis and antitumoractivity of novel pyrido[2,3-d][1,2,4]triazoIo[4,3_a] pyrimidin_ S-one derivatives; Eur. J. Med. Chem. 46,203].-2036 (2010) [3] S, M. El-MoghazY, D. A. lbbahim, N. M. Abdelgawad, N. A. H. Farag, A. s. E!_Khouly; Design, synthesis and biologicaI evaluation of noveI pyrimido[J,5-d]pyrimidine CDK2 inhibitors as anti-tumor agents; Scie ntia P ha rma ce utica, 7 9, 429447 |zOtL) [4] M.Y. Gavrilov, t. G. Mardanova, V. E. Kolla, M. E. Konshin, Synthesis and anti-inflammatory and

analgesic activities of 2-aryIamino-5,6,7,8-tetrahydroquinoline-3-carboxamid (1988)

es;

pharm. Chem. J

.22,554

[5] Abdel-Rahman B. A. El-G azzar, Hend N. Hafez; Synthesis of 4-substituted pyrido[2,3-d]pyrimidina(lH)one as analgesic and anti-inflammatory agents; Bioorg. Med. Chem. Lett., Lg,3392 (2009).

Lista Autorów Abd El-Galil E. Amr Adamek J. Andrijewski Grzegorz Antoszczak Michał Bajerlein Dawid Bałczewski piotr Banach Anna Banbura J. Baraniak Janina

Barczyński Piotr Bartkowiak Grńyna Bartos paulina

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P_063 PĄ24

P-088

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Bączek Natalia

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Bednarska M. Bernasińska Joanna Bester karol

P_030

Bąkowicz Julia

BłaużAndrzej Bojarski Andrzej J. Boratyński Przemysław

Branowska Danuta

Brodzka Anna Budzisz Elźbieta Bukowski wiktor Cal Dariusz Cegłowski Michał Celeda M. celewicz Lech chworos Arkadiusz Ciastek Sylwia Ciechńska Magdalena

ciesielski witold

Cofta Grzegorz Cypryk Marek czarnacka oliwia czekanski Łukasz Dąbkowski Wojciech Demchuk Oleg M. Deredas Dariusz Deska Małgorzata Dina H. Elngar Dorsz Mateusz Drabowicz Józef Dresler Ewa Duszyńska Beata

Dziubą K.; Dziwiński Bartosz

Fenyk Anna

Filapek Michał Flamholc Rafał Flis, A Frński Rafał Fusiarz Iwona Gadzinowska K. Gajda Anna Gajda Tadeusz

Gawron Katarzyna Gębicki K. Gierczyk Błażej Głowacka lwona E. Golimowska Magdalena Gostyński Bartłomiej Gotkowska Joanna Grabkowska-Druzyc Magdalena Grudzka Iwona Grymel M. Grzegożek Maria

Guga Piotr

Guziejewski Dariusz

P-073

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Lista uczestników Adamek Jakub

j aku b.

Bartkowiak Gralyna Bartos paulina

n

Bujnicki Bogdan

UniwersytetŁódzki

CBMiM PAN

chemikł[email protected] Oleh.Demchuk@UMCS. dari usz. deredas@p. lodz.

[email protected]

Drabowicz lozef

Uniwersyet im. Adama Mickiewicza

[email protected]

Dziuba kamil Flamholc Rafał

p

l

CBMiM PAN

l

Inst;rtut

Tadeusz E. Golimowska Magdalena Gostynski Bartłomiej Gotkowska Joanna

ńał

Janecki Tomasz

Szymon tut*.in Jasiński Radomir Jarryński

Jasiński

.1_11'=*'f";da@v,lodz,v| lwona,glowacka@umed,lodz.pl

PolitechnikaŁódzka

l76280@student,pwr,wroc,pl

Uniwersytet Medyczn y w Łodzi

fffi:ff trffi,]l'ilT:ólu*.a. .

twonagrudzka@gmail,com

magre@indY,chemia,pk,edu.pl

T:T*'@uni,lodzpl

:""Bffi3irr' tjanecki@p,lodz,pl [email protected] mj,asin,st,@uni,lodz,pl

Ka@rryna ;iT'ó$Hiilj;l"r'

Jaszczewska Joan Jaśkowska

rolunrlu

Kahrryna Kaczmarek n"nutu Kapłon Katarąyna

politechnika

,lT'or'.;:[email protected]

Magdalena

ff:*"*:":-ryc Grzegozek Maria Ignaczak Anna Jaklińska Magdalena

Cięzkiej Syntery Organicznej

.Blachownia" Uniwersytet Marii Curie-Skłodowskiej UniwersytetŁódzki politechnikaŁódzka

ravcrane@oL,pl

Gajda

wrocławska

CBMiM PAN loa, pl

Uniwersytet Medyczn y w Łodzi Uniwersytet Medyczrr y w Łodzi Uniwersytet Ślą5ti

politechnika

krakowska

Uniwersytet Łódzki Uniwersytet Mari i Curie-Skłodowskiej

politechnikaŁódzka politechnika

Łódzka

Uniwersytet Łódzki

Łód?ki

Uniwersytet

politechnika

!

krakowska

[email protected]

CBMiM PAN

jolanta,bazan6@gmail,com

pol itechnika

Adamed sp. z o.o.

krakowska

Uniwersytet Mari i Curie-Skłodowskiej

.."*'YnujusĘ[email protected] [email protected] [email protected]

Karpowicz Rafał Kędzia Jacek

ifar3@interia,pl

Kiełbasiński

11':|,!io,ia@p,lodz,pl

Anna Koprowski Marek

politechnikaŁódzka

AJD w Częstochowie

anna-gajda@P,lodz,pl

Głowacka Iwona

[:i:,il.l**"''""

Uniwersytet Marii CurieSkłodowskiej

[email protected]

-

Piotr Nututiu

CBMiM PAN

Lubl in.pl

dĘ@cbmm.lodzpl

Dresler Ewa

Komasa

Uniwersytet Łódzki

Uniwersyet im. Adama Mickiewicza

[email protected]

Deska Małgorzata

Kleczewsku

CBMiM PAN

[email protected]

Demchuk oleh Deredas Dariusz

Justyna

Inst;ćut Chemii Organiczrrej PAN Uniwersytet Medyczrr w Łodzi l

pl

[email protected]

czekanski Łukasz Dąbkowski Wojciech

Jolanta pisklak

l

Iodz.

ceglowski. [email protected]

Cierpiał Tomasz

Jastrzębska

p

[email protected]

Ciechanska Magdalena

Jakubowski

politechnikaŁódzka politechnikaŁódzka

pl

[email protected]

Cal Dariusz Cegłowski Michał

Anna

atal i ą bac [email protected] dz.

anną brodzka@icho. edu. e lzb ietą bu dńsz@umed.

Budzisz Elżbieta

Gajda

Politechnika Śq5ka Uniwersyet im. Adama Mickiewicza

[email protected]

Bączek Natalia Brodzka Anna

.

adamek@polsl. pl

[email protected]

[email protected]

[email protected] [email protected]| źrniak@amu,edu,pl

[email protected]

UniwersytetŁódzki

CBMiM PAN Uniwersyet Marii Curie-Skłodowskiej Uniwersytet Łódzki

politechnikaŁódzka

CBMiM PAN Uniwersytet im. Adama Mickiewicza

pol itechn

ika wrocławska

Uniwersytet Medyczrr y w Łodzi Uniwersytet im. Adama

CBMiM PAN

Mickiewicza