CS196618B1 - Derivatives of pyridine-4-carboxyhydrazide with potential antitubercular and antitumour actions and method for their preparing - Google Patents
Derivatives of pyridine-4-carboxyhydrazide with potential antitubercular and antitumour actions and method for their preparing Download PDFInfo
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- CS196618B1 CS196618B1 CS462676A CS462676A CS196618B1 CS 196618 B1 CS196618 B1 CS 196618B1 CS 462676 A CS462676 A CS 462676A CS 462676 A CS462676 A CS 462676A CS 196618 B1 CS196618 B1 CS 196618B1
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- pyridine
- derivatives
- carboxhydrazide
- methoxyphenyl
- potential
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- 230000002365 anti-tubercular Effects 0.000 title claims description 5
- 230000000259 anti-tumor effect Effects 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- -1 ketone compounds Chemical class 0.000 claims description 14
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical class NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 7
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 2
- 241000186365 Mycobacterium fortuitum Species 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- CXOKVBPWTHFGTN-UHFFFAOYSA-N 3-[(2-hydroxyphenyl)methylidene]chromene-2,4-dione Chemical compound OC1=CC=CC=C1C=C1C(=O)C2=CC=CC=C2OC1=O CXOKVBPWTHFGTN-UHFFFAOYSA-N 0.000 description 1
- PJKDVDQLFSFEBL-UHFFFAOYSA-N 4-hydroxy-3-(3-oxo-1,3-diphenylpropyl)chromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=CC=CC=1)CC(=O)C1=CC=CC=C1 PJKDVDQLFSFEBL-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- AFWKBSMFXWNGRE-ONEGZZNKSA-N Dehydrozingerone Chemical compound COC1=CC(\C=C\C(C)=O)=CC=C1O AFWKBSMFXWNGRE-ONEGZZNKSA-N 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- AFWKBSMFXWNGRE-UHFFFAOYSA-N dehydrozingerone Natural products COC1=CC(C=CC(C)=O)=CC=C1O AFWKBSMFXWNGRE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001005 tuberculin Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005740 tumor formation Effects 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
REPUBLIKA SOCIALISTICKÁ ČESKOSLOVENSKA (19) POPIS VYNÁLEZUK AUTORSKÉMU OSVEDĚENIU 196618 (11) (B1) (51) Int. Cl.3 (22) Přihlášené 13 07 76(21) (PV 4626-76) C 07 D 213/06 ÚŘAD PRO VYNÁLEZY A OBJEVY (40) Zverejnené 31 07 79 (45) Vydané 30 05 82 (75)
Autor vynálezu PROKSA BOHUMIL, ing., HOLIČ f '
FUŠKA JÁN, ing., CSc., a FUSKOVÁ ALŽBĚTA, ing., BRATISLAVA (54) Deriváty pyridín-4-karboxhydrazidu s potenciálnymi antituberkulóznymia protinádorovými účinkami a sposob ich přípravy
Vynález sá týká niektorých nových derivátovpýridín-4-karboxhydrazidu (INH) ako potenciál-nych tuberkúlostatík a kancerostatík a spósobuich přípravy.
Potenciálny protinádorový účinok niektorýchderivátov INH sledoval J. P. Matvejčuk (Vopr.eksp. onkol. 3/1968/101) a zistil, že niektoré z nichinhibovali tvorbu tumorov. Pri hodnotení biologic-kých účinkov inej skupiny derivátov INH Μ. I. Col-nághi, G. Dellá Porte á L. Parmí (Tumpri 55/1969//309) zistili, že samotný INH nepotláča tvorbufhádorov, žatiaí čo L. D. Jones, D. G. pajrchilda W. C. Morse (Am. Rev. Resp. Dis., 103/1^71/612)potvrdili potenciálny karcinogénny účinql^hlpkto-rých derivátov INH. F. Lacour, G. Oberling aM. Guerin (Bull. Ass. Franc. Cancer 44/1957/88)zistili,. že antikoagulanciá typu kumarínu inhibo-vali rast niektorých nádorov u experimentálnychzvierat, pričam tieto látky znižujú tvorbu metastázv prúcach a v pečeni zvierat, ako to potvrdili vosvojich prácach D. Agostino, E. E. Cliffton, A. Gi-rolamo (Cancer 19/1966/284), M. Lawinski a spok(Arch. Immunol. Ther. Exp.', 19/1971/532) azvyšujúšúčasné prežívanie pokusných zvierat, ako. udá*vajú vo svojich výsledkách S. Wood, E. D. Holyákea J. H. YardJey (Canad.Conf. Cancer 4/1961/223). A. L. Cetlin a spol, (Tr. Bot. Inst. AN ZSSR 5,No. 16/1972/7) popísali cytotoxický účinok niekto-rých prírodných derivátov kumarínu na buňky ná- dorov, R. A.' Finnegan, K. E. Merkel a N. Back(J. Pharm. Sci. 61/19^2/1599) účinok syntetickýchkumarínov na S-180.
Lespagnol A. a spol. (Bull. Soc. Pharm. Lilie1/1955/30), Η, H. Fox a J. T. Gibas (J. Org. Chem;18/1953/983), P. P. T. Sah a S. A. Pepples (J. Am.Pharm. Áss,,i 43/1954/513). připravili deriváty, pyri-,dín-4-karboxhydrazidu so 4-fenyl-3-butén-27onoma mnohými ďalšími karbonylovými zlúčeninami,avšak tieto látky vykazovali v pokusech; iba malý.antituberkulózny efekt.
Deriváty pyri^ín-4-karboxhydrazidu s potenciál-nyrr^i antituberkulóznymi a potinádorovýml účin-kami obecnéřto vzorca I kdeaR..je -a; .
-R
R pričorfi Rj znamená metyl alebo fenyl, R2 znamená
-CH-GH 19661 8 196618 alebo
kde R3 znamená hydroxy alebo metoxy skupinu,alebo R,- CH 0 Ί A JSr
kde R4 znamená hydroxyfenyl, alebo metoxyfenyl,sa pripravujú kondenzáciou pyridín-4-karbox-hydrazidu s ketozlůčeninami obecného vzorca II
kde Rt a R2 znamená to isté, ako už bolo uvedené,alebo s ketozlůčeninami obecného vzorca III
kde R4 znamená hydroxyfenyl alebo metoxyfenyl,v prostředí polárného, alebo semipolárneho roz-púšťadla a výsledný produkt sa izoluje kryštali-záciou. Příklad 1 Příprava látky č. 1 4-(4-hydroxy-3-metoxyfenyl)-2--pyridín-4-karboxhydrazón-3-buténu j: ¾ , C17H17N3O6 m. v. 311,340,18 g (1,3 mM) pyridín-4-karboxhydrazidu (SPO-FA, Praha) rozpuštěných v 2 ml 50% vodnéhoetanolu sa přidalo k 0,25 g (1,3 mM) 4-(4-hydroxy--3-metoxyfenyl)-3-butén-2-ónu syntetizovanéhoz vanilínu a acetonu podfa Mc Gookin A., Sin-clair D. C. J. Chem, Soc., (1928/1170), v 2 ml50% vodného etanolu. Zmes sa zahriala do varua nechala krištalizovať. Látka sa prekryštalizovalaz 50% vodného etanolu a vákuovo vysušila. Získa-lo sa 0,20 g (0,6 mM) 4-(4-hydroxy-3-metoxyfenyl)--2-pyridín-4-karboxhydrazón-3-buténu, b. t. 171až 172,5 °C, UV Amax: 264 a 204 nm v etanole. Příklad 2 Příprava látky č. 2 1,3-difenyl-1-(pyridín-4-kar-boxhydrazón)-2-propénu C21H17N3O m. v. 327,39K 0,65 g (3,12 mM) 1,3-difenyl-2-propén-1-ónupřipraveného z acetofenónu a benzaldehydu po-dl'a E. P. Kohler, Η. M. Chadwell., Org. Syntheses,Col. Vol, I, (1941/78) v 5 ml 2-propanolu sa při-dalo 0,45 g (3,28 mM) pyridín-4-karboxhydrazidu(SPOFA, Praha) a zmes sa zahrievala do rozpuste-nia tuhých zložiek; na chladnom mieste vykrišta-lizovaná látka sa rekryštalizovala z 80% vodnéhoetanolu. Získalo sa 0,50 g (1,5mM) 1,3-difenyl-1--(pyridín-4-karboxhydrazón)-2-propénu, b. t. 141až 142°C, UVAmax: 240 a 204 nm v etanole, IČ:3400, 3300, 2950, 1680, 1590, 1540, 1490, 1450,1400, 1360, 1280, 1050, 980, 820 cm~1 v chloro-forme. Příklad 3 Příprava látky č. 3 1,3-difenyl-1-(pyridín-4-karbox-hydrazón)-3-(4-hydroxykumarin-3-yl)-propánu C30H23N3O4 m. v. 441,540,9 g (2,42 mM) 1,3-difenyl-1-(4-hydroxykumarin--3-yl)-propán-3-ónu (získaný reakciou 4-hydroxy-kumarínu s 1,3-difenyl-2-propén-1-ónu, Ikawa M.,a spol., J. Am. Chem. Soc., 66 (1944/902) v 5 ml2-propanolu sa zmiešalo s 0,34 g (2,5 mM) pyri-dín-4-karboxhydrazidu (SPOFA, Praha) a zahrialasa do rozpustenia tuhých častíc. Zmes sa nechalakrystalizovat’ a vylúčené kryštály (0,11 g) nezrea-govaného pyridín-4-karboxhydrazidu sa odsáli.Z matečného luhu sa vákuovo oddestilovalo roz-púšťadlo a zbytok sa trikrát rekryštalizoval z 94%etanolu. Po vysušení sa získalo 0,62 g (1,40 mM)1,3-difenyl-1-(pyridín-4-karboxhydrazón)-3-(4-hyd-roxykumarin-3-yl)-propánu, b. t. 139 až 141 °C,UVAmax 303, 289, 239, 207 nm v etanole, IČ: 3700,3300, 2990, 1690, 1610, 1550, 1480, 1450, 1400,1370, 1310, 1250, 1190, 1060, 920 cm"1 v chloro-forme. Příklad 4 Příprava Jatky č. 4 1-(4-hydroxy-3-metoxyfenyl)-1-- (4 -hydroxykumarin-3-yl) -3- (pyridín-4-karboxhyd-razónj-butánu C2fiH23N3Oý m. v. 473,48, 2,0 g (6,4 mM) 3-J 1-(4-hydi£oxy-3-metoxyfenyl)-3--oxobutylJ-4-hydroxykumarínu (získaný reakciou1(-4-hydroxy-3-metoxyfenyl)-3-oxobuténu-1 s 4--hydroxykumarínu, Ikawa M., a spol., J. Am. Chem.Soc., 66 (1944/902) a 0,88 g (6,4 mM) pyridín-4--karboxhydrazidu (SPOFA, Praha) sa zahrievalov 15 ml dioxánu do úplného rozpustenia. Po vy-chladnutí z roztoku vypadávajú kryštály, ktoré po2násobnej rekryštalizácii z 2-propanolu poskytli1,8 g (3,6 mM) 1-(4-hydroxy-3-metoxyfenyl)-1-(4--hydroxykumarin-3-yl) - 3 - (pyridin - 4 -karboxhydra-zón)-butánu, b. t.. 208 až 209 °C, UVAmax 345, 250a 204 nm v metanole, IČ: 3700, 3550, 3000, 1680,1660, 1630, 1595, 1500, 1410, 1360, 1250, 950 cm"1 v chloroforme. 1 966 1 8 P r í k I a d 5 Příprava látky č. 5 3-(2-hydroxybenzal)-4-(pyridín--4-karboxhydrazón)-2-oxochromanu C22H15N3O4 m. v. 385,39Zmes 0,50 g (1,8 mM) 3-(2-hydroxybenzal)-2,4-di-ketochromanu (syntetizovaný z 4-hydroxykumarínua salicylaldehydu, Sullivan W. R., a spol., J. Am.Chem. Soc., 65 (1943/2288) a 0,25 g (1,8 mM)pyridín-4-karboxhydrazidu sa zahrievalo v 6 ml2-propanolu do rozpustenia zložiek. Na chladnommieste vykríštalizovala látka, ktorá po trojnásob-nej rekryštalizácii z 2-propanolu poskytla 0,22 g(0,5 mM) 3-(2-hydroxybenzal)-4-pyridín-4-karbox- hydrazón-2-oxochromanu, b. t. 243 až 245 °C,UVAmax: 334, 296, 288, 238, 214 nm v metanole.Potenciálny protinádorový účinok bol hodnotenýna základe inhibície značkovaných prekurzorovdo buniek Ehrlichov ascitový karcinom a LeukémiaP-388 in vitro metodou, ktorú popísali J. Fuškaa spol. (Neoplasma 18/1971/631), antituberkulóznyúčinok bol hodnotený na dva kmene TBC: Myo-bacterium tuberculosis BCG a Mycobacteriumfortuitum. Účinok niektorých látok na jednotlivé modelyje uvedený v tabuTke 1. 1 96618
Inhibícia rastu M. tuberculosis .... ... gCQ M. fortuitum σι 3. 25 o 40 m m Inhibícia využitia ”Cprekurzoru (%) P-388 A V O) =í. o o 6,0 59,3 42,0 OJ 32,0 30,0 EAC A V 4,0 24,0 49,6 13,0 20,0 47,8 Testovaná látka *» 1 X S ° X o n X Λ O 5-i B Ť X z 1 o o é z X z 1 oo . i z O X / \ CK ° 1 X z 1 o o έ z Číslo látky - OJ co
Claims (2)
196618 PREDMET VYNÁLEZU
1. Deriváty pyridín-4-karboxhydrazidu s poten-ciálnymi antituberkulóznymi a protinádorovýmiúčinkami obecného vzorca I
2. Spósob přípravy derivátov pyridín-4-karbox-hydrazidu pódia bodu 1, vyznačujúci sa tým,že sa kondenzuje pyridín-4-karboxhydrazids ketozlúčeninami obecného vzorca II. kde R je \NH-N: pričom Ri znamená metyl alebo fenyl,R2 znamená CH=»CH o—c Ř« II kde R1 znamená metyl alebo fenyl, R2 znamená _CH=«GH alebo alebo
kde R3 znamená hydroxy alebo metoxy skupi-nu, ale s ketozlúčeninami obecného vzorca III kde R3 znamená hydroxy alebo metoxy skupinu,alebo rm- ch .o III
kde R4 znamená hydroxyfenyl, alebo meťóxy-fenyl. i kde R4 znamená hydroxyfenyl, alebo metoxy-fenyl, v prostředí polárného alebo semipolár-nehovfozpúšťadla a výsledný produkt sa izo-luje kjyštalizáciou. MTZ O 21 82 Cena: 2,40 Kčs 196618 $ 40 & m 47,9 2,8 o o Γ" ci v·“ o T— + o l< CM K Ό 15,0 O Λ Z\ i C / X **?x 1o—o 1 z 1 X Ť > o 7 s ii o Φ M- m c Έ > _4 I > c Έ <u “O o I < *0) s o c T) o .c Φ c I Ό.
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| CS462676A CS196618B1 (en) | 1976-07-13 | 1976-07-13 | Derivatives of pyridine-4-carboxyhydrazide with potential antitubercular and antitumour actions and method for their preparing |
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| CS196618B1 true CS196618B1 (en) | 1980-03-31 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103601711B (zh) * | 2013-11-04 | 2016-09-07 | 广东中烟工业有限责任公司 | 一种香豆素衍生物及其制备方法和应用 |
-
1976
- 1976-07-13 CS CS462676A patent/CS196618B1/cs unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103601711B (zh) * | 2013-11-04 | 2016-09-07 | 广东中烟工业有限责任公司 | 一种香豆素衍生物及其制备方法和应用 |
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