MD4125C1 - Compuşi 1,3,4-oxadiazolici cu proprietăţi antituberculoase conţinând tiouree monosubstituită - Google Patents
Compuşi 1,3,4-oxadiazolici cu proprietăţi antituberculoase conţinând tiouree monosubstituită Download PDFInfo
- Publication number
- MD4125C1 MD4125C1 MDA20100103A MD20100103A MD4125C1 MD 4125 C1 MD4125 C1 MD 4125C1 MD A20100103 A MDA20100103 A MD A20100103A MD 20100103 A MD20100103 A MD 20100103A MD 4125 C1 MD4125 C1 MD 4125C1
- Authority
- MD
- Moldova
- Prior art keywords
- thiourea
- compounds
- antituberculous
- oxadiazole compounds
- properties
- Prior art date
Links
- -1 monosubstituted thiourea Chemical class 0.000 title claims abstract description 14
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 title claims abstract description 6
- 230000002365 anti-tubercular Effects 0.000 title abstract description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 9
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 20
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 3
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000005915 ammonolysis reaction Methods 0.000 abstract description 2
- 238000006698 hydrazinolysis reaction Methods 0.000 abstract description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 abstract description 2
- 229960002447 thiram Drugs 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 230000009036 growth inhibition Effects 0.000 abstract 1
- 238000006177 thiolation reaction Methods 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 229910052729 chemical element Inorganic materials 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HHRALRRIPHUDEN-UHFFFAOYSA-N [4-(5-benzylsulfanyl-1,3,4-oxadiazol-2-yl)phenyl]thiourea Chemical compound C1=CC(NC(=S)N)=CC=C1C(O1)=NN=C1SCC1=CC=CC=C1 HHRALRRIPHUDEN-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- YTGQRSFSVIBQEN-UHFFFAOYSA-N [4-[5-(pyridin-4-ylmethylsulfanyl)-1,3,4-oxadiazol-2-yl]phenyl]thiourea Chemical compound C1=CC(NC(=S)N)=CC=C1C(O1)=NN=C1SCC1=CC=NC=C1 YTGQRSFSVIBQEN-UHFFFAOYSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 201000008827 tuberculosis Diseases 0.000 description 5
- DKLKJBLSGAINPQ-UHFFFAOYSA-N [4-[5-[2-(2,4-dichlorophenyl)-2-oxoethyl]sulfanyl-1,3,4-oxadiazol-2-yl]phenyl]thiourea Chemical compound C1=CC(NC(=S)N)=CC=C1C(O1)=NN=C1SCC(=O)C1=CC=C(Cl)C=C1Cl DKLKJBLSGAINPQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VBGZBLOXMSJIRP-UHFFFAOYSA-N 5-(4-isothiocyanatophenyl)-3h-1,3,4-oxadiazole-2-thione Chemical compound C1=CC(N=C=S)=CC=C1C1=NNC(=S)O1 VBGZBLOXMSJIRP-UHFFFAOYSA-N 0.000 description 2
- 241001646725 Mycobacterium tuberculosis H37Rv Species 0.000 description 2
- 108700035964 Mycobacterium tuberculosis HsaD Proteins 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 2
- 229960001225 rifampicin Drugs 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- MGEPFQZVVFAFKA-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-[[5-(4-isothiocyanatophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CSC1=NN=C(C=2C=CC(=CC=2)N=C=S)O1 MGEPFQZVVFAFKA-UHFFFAOYSA-N 0.000 description 1
- OLVRTTZNNXZFMK-UHFFFAOYSA-N 2-benzylsulfanyl-5-(4-isothiocyanatophenyl)-1,3,4-oxadiazole Chemical compound C1=CC(N=C=S)=CC=C1C(O1)=NN=C1SCC1=CC=CC=C1 OLVRTTZNNXZFMK-UHFFFAOYSA-N 0.000 description 1
- ZKFWLDORQWOSHF-UHFFFAOYSA-N 2-chloro-n-[5-[2-(4-chloroanilino)-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CSC(S1)=NN=C1NC(=O)C1=CC=CC=C1Cl ZKFWLDORQWOSHF-UHFFFAOYSA-N 0.000 description 1
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
- HTDLSAGEOYDVSJ-UHFFFAOYSA-N 4-phenyloxadiazole Chemical compound O1N=NC(C=2C=CC=CC=2)=C1 HTDLSAGEOYDVSJ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001355 anti-mycobacterial effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- KNDXZFMNQKSIHU-UHFFFAOYSA-N methyl 2,3,5,6-tetrachloro-4-methylsulfanylcarbonylbenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)SC)C(Cl)=C1Cl KNDXZFMNQKSIHU-UHFFFAOYSA-N 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20100103A MD4125C1 (ro) | 2010-09-17 | 2010-09-17 | Compuşi 1,3,4-oxadiazolici cu proprietăţi antituberculoase conţinând tiouree monosubstituită |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20100103A MD4125C1 (ro) | 2010-09-17 | 2010-09-17 | Compuşi 1,3,4-oxadiazolici cu proprietăţi antituberculoase conţinând tiouree monosubstituită |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4125B1 MD4125B1 (en) | 2011-08-31 |
| MD4125C1 true MD4125C1 (ro) | 2012-03-31 |
Family
ID=45815251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20100103A MD4125C1 (ro) | 2010-09-17 | 2010-09-17 | Compuşi 1,3,4-oxadiazolici cu proprietăţi antituberculoase conţinând tiouree monosubstituită |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4125C1 (mo) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ306408B6 (cs) * | 2014-12-11 | 2017-01-11 | Univerzita Karlova v Praze, Farmaceutická fakulta v Hradci Králové | Dinitrofenyloxadiazol nebo -triazol, jeho použití a farmaceutický přípravek ho obsahující |
| MD4404C1 (ro) * | 2015-03-18 | 2016-09-30 | Институт Химии Академии Наук Молдовы | Compusul 2-(propiltio)-5H-[1,3,4]tiadiazolo[2,3-b]chinazolin-5-onă, care manifestă activitate antituberculoasă şi procedeu de sinteză a acestuia |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB729891A (en) * | 1952-10-10 | 1955-05-11 | Bayer Ag | New 4,5-dihydro-1,3,4-oxadiazol-5-one derivatives |
| GB925911A (en) * | 1960-07-28 | 1963-05-15 | Ed Geistlich Sohne A G | Antitubercular pharmaceutical compositions |
| JPH07258234A (ja) * | 1994-03-17 | 1995-10-09 | Shiratori Seiyaku Kk | １，３，４−オキサジアゾール−２（３ｈ）−チオン類の製造法 |
| MD613G2 (ro) * | 1994-02-24 | 1997-06-30 | Государственный Университет Молд0 | Procedeu de obţinere a 2-mercapto-1,3,4-oxadiazolilor |
| MD4009C2 (ro) * | 2008-07-15 | 2010-08-31 | Институт Химии Академии Наук Молдовы | Utilizarea 1-metil-4-(N-metilaminobutil-4)-β-carbolinei în calitate de remediu antituberculos |
-
2010
- 2010-09-17 MD MDA20100103A patent/MD4125C1/ro not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB729891A (en) * | 1952-10-10 | 1955-05-11 | Bayer Ag | New 4,5-dihydro-1,3,4-oxadiazol-5-one derivatives |
| GB925911A (en) * | 1960-07-28 | 1963-05-15 | Ed Geistlich Sohne A G | Antitubercular pharmaceutical compositions |
| MD613G2 (ro) * | 1994-02-24 | 1997-06-30 | Государственный Университет Молд0 | Procedeu de obţinere a 2-mercapto-1,3,4-oxadiazolilor |
| JPH07258234A (ja) * | 1994-03-17 | 1995-10-09 | Shiratori Seiyaku Kk | １，３，４−オキサジアゾール−２（３ｈ）−チオン類の製造法 |
| MD4009C2 (ro) * | 2008-07-15 | 2010-08-31 | Институт Химии Академии Наук Молдовы | Utilizarea 1-metil-4-(N-metilaminobutil-4)-β-carbolinei în calitate de remediu antituberculos |
Non-Patent Citations (8)
| Title |
|---|
| Chang Hoon Lee, Hyun In Cho, and Kee-Jung Lee. Bull. Korean Chem. oc. 2001, vol.22, No. 1153 (regăsit în Internet la 2011.05.12, url: http://pdf.easechem.com/pdf32/f0038874-65de-4d17-ad40-5ca8992fa8b7.pdf) * |
| Chang Hoon Lee, Hyun In Cho, and Kee-Jung Lee. Bull. Korean Chem. Soc. 2001, Vol. 22, No. 10 1153 (regăsit în Internet la 2011.05.12, url: http://pdf.easechem.com/pdf/32/f0038874-65de-4d17-ad40-5ca8992fa8b7.pdf ) * |
| Fliur Macaev, Ghenadie Rusu, Serghei Pogrebnoi, Alexandru Gudima, Eugenia Stingaci, Ludmila Vlad, Nathaly Shvets, Fatma Kandemirli, Anatholy Dimoglo, and Robert Reynolds. Bioorganic & Medicinal Chemistry, Volume 13, 2005, p. 4842-4850 * |
| Gabriel Navarrete-Vázquez, Gloria Marı´a Molina-Salinas, Zetel Vahi Duarte-Fajardo, Javier Vargas-Villarreal, Samuel Estrada-Soto, Francisco González-Salazar, Emanuel Hernández-Núñez, Salvador Said-Fernández. Bioorganic & Medicinal Chemistry, Volume 15, Issue 16, 15 August 2007, p. 5502-5508 * |
| Hamish S. Sutherland, Adrian Blaser, Iveta Kmentova, Scott G. Franzblau, Baojie Wan, Yuehong Wang, Zhenkun Ma, Brian D. Palmer, William A. Denny, and Andrew M. Thompson. J. Med. Chem. 2010, 53, pp. 855-866. * |
| Harish Rajak, Murli Dhar Khary and Pradeep Mishra. International Journal of Pharmaceutical Sciences and Nanotechnology. 2009, vol. 2, issue 1, p.390. (regăsit în Internet la 2011.05.12, url: http://ijpsnonline.com/Issues/310.pdf ) * |
| Harish Rajak, Murli Dhar Khary and Pradeep Mishra. International Journal of Pharmaceutical Sciences and Nanotechnology. 2009, vol. 2, issuie 1, p390. (Regăsit în Internet la 2011.05.12, url: http://ijpsnonline.com/Issues/310.pdf ) * |
| Rusu, G. G.; Gutu, E. E.; Barba, N. A. Russ. J. Org. Chem. 1995, vol. 31, p. 1721. * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4125B1 (en) | 2011-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |