IT1146724B - Purine and pyrimidine cpds. - Google Patents
Purine and pyrimidine cpds.Info
- Publication number
- IT1146724B IT1146724B IT68583/81A IT6858381A IT1146724B IT 1146724 B IT1146724 B IT 1146724B IT 68583/81 A IT68583/81 A IT 68583/81A IT 6858381 A IT6858381 A IT 6858381A IT 1146724 B IT1146724 B IT 1146724B
- Authority
- IT
- Italy
- Prior art keywords
- cpds
- adenine
- guanine
- iii
- purine
- Prior art date
Links
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title abstract 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title abstract 3
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 abstract 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 4
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 abstract 4
- 229930024421 Adenine Chemical group 0.000 abstract 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical group NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 abstract 3
- 229960000643 adenine Drugs 0.000 abstract 3
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical group OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 abstract 2
- 239000003443 antiviral agent Substances 0.000 abstract 2
- 229940104302 cytosine Drugs 0.000 abstract 2
- -1 monomethoxytrityl Chemical group 0.000 abstract 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 abstract 2
- 229940035893 uracil Drugs 0.000 abstract 2
- ZADISRFYMTWQNC-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methoxy]propane-1,3-diol Chemical compound NC1=NC=NC2=C1N=CN2COC(CO)CO ZADISRFYMTWQNC-UHFFFAOYSA-N 0.000 abstract 1
- MFEFTTYGMZOIKO-UHFFFAOYSA-N 5-azacytosine Chemical group NC1=NC=NC(=O)N1 MFEFTTYGMZOIKO-UHFFFAOYSA-N 0.000 abstract 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical group FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 abstract 1
- 241000700584 Simplexvirus Species 0.000 abstract 1
- 241000711975 Vesicular stomatitis virus Species 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 229940121357 antivirals Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000007541 cellular toxicity Effects 0.000 abstract 1
- 229960002949 fluorouracil Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 231100000086 high toxicity Toxicity 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 210000004962 mammalian cell Anatomy 0.000 abstract 1
- MXSMRDDXWJSGMC-UHFFFAOYSA-N n-(6-oxo-3,7-dihydropurin-2-yl)acetamide Chemical group N1C(NC(=O)C)=NC(=O)C2=C1N=CN2 MXSMRDDXWJSGMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000003128 rodenticide Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 abstract 1
- 229940113082 thymine Drugs 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 241000712461 unidentified influenza virus Species 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
(A) Purine and pyrimidine cpds. of formula (I) are new, where X is a uracil, 5-fluorouracil, cytosine, 5-azacytosine, adenine, guanine or 2-N-acetylguanine gp.; and R and R1 are H, benzyl, monomethoxytrityl or t-butyldimethylsilyl. Provided that the cpd. is not 9-((2-hydroxy-1-hydroxy methylethoxy) methyl) adenine (II)). (B) Purine and pyrimidine cpds. of formula (III) are new. (B and B' are adenine, cytosine, thymine, guanine or uracil gps.; either Z and Y are each CH2, or Z and Y together form CH-CH2-CH to complete a deoxyribose ring and similarly for Z' and Y', except that only one deoxyribose ring may be present; Q is O, S or a bond; and R2-R4 are H, 1-6C alkyl opt. substd. by Ph or halogen, monomethoxytrityl or opt. substd. silyl). (C) use of (III) as an antiviral agent is new. Cpds. (I)-(III) have antiviral activity, often with low cell toxicity. Typical cpds. are active against Herpes simplex virus, influenza virus and vesicular stomatitis virus. Some cpds. have high toxicity to mammalian cells even at low dosages and so are useful as rodenticides and insecticides. Generally cpds. in which R and/or R1 is H and B is an adenine or guanine gp. are antivirals without undue toxicity, while cpds. in which R and R1 are both other than H are toxic. Dose is 0.1-100 mg/kg. 2-4 times daily.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT68583/81A IT1146724B (en) | 1981-12-04 | 1981-12-04 | Purine and pyrimidine cpds. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT68583/81A IT1146724B (en) | 1981-12-04 | 1981-12-04 | Purine and pyrimidine cpds. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IT8168583A0 IT8168583A0 (en) | 1981-12-04 |
| IT1146724B true IT1146724B (en) | 1986-11-19 |
Family
ID=11309933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT68583/81A IT1146724B (en) | 1981-12-04 | 1981-12-04 | Purine and pyrimidine cpds. |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1146724B (en) |
-
1981
- 1981-12-04 IT IT68583/81A patent/IT1146724B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IT8168583A0 (en) | 1981-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19981231 |