FR2197570A1 - Esters of penicillins with hydroxychalcones - with higher antibacterial activity than the parent penicillins - Google Patents
Esters of penicillins with hydroxychalcones - with higher antibacterial activity than the parent penicillinsInfo
- Publication number
- FR2197570A1 FR2197570A1 FR7230605A FR7230605A FR2197570A1 FR 2197570 A1 FR2197570 A1 FR 2197570A1 FR 7230605 A FR7230605 A FR 7230605A FR 7230605 A FR7230605 A FR 7230605A FR 2197570 A1 FR2197570 A1 FR 2197570A1
- Authority
- FR
- France
- Prior art keywords
- penicillins
- esters
- hydroxychalcones
- antibacterial activity
- parent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229930182555 Penicillin Natural products 0.000 title abstract 6
- 150000002960 penicillins Chemical class 0.000 title abstract 5
- UDOOPSJCRMKSGL-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one Chemical class OC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 UDOOPSJCRMKSGL-UHFFFAOYSA-N 0.000 title abstract 3
- 150000002148 esters Chemical class 0.000 title abstract 3
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Esters of penicillins or penicillanic acids with hydroxychalcones, esp. of formula (I): (where R1 and R2 are H, halogen, alkyl or NO2; and R3 is an acyl residue as found in known penicillins), have higher antibacterial activity than the corresp. unesterified penicillins. The esters are pref. prepd. by reacting an opt. substd. p-hydroxybenzaldehyde with acetophenone and using the resulting hydroxychalcone to esterify a penicillin.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7230605A FR2197570A1 (en) | 1972-08-29 | 1972-08-29 | Esters of penicillins with hydroxychalcones - with higher antibacterial activity than the parent penicillins |
| DE19732341514 DE2341514A1 (en) | 1972-08-29 | 1973-08-16 | NEW PENICILLINESTERS, PROCESS FOR MANUFACTURING THE SAME AND CONTAINING MEDICINAL PRODUCTS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7230605A FR2197570A1 (en) | 1972-08-29 | 1972-08-29 | Esters of penicillins with hydroxychalcones - with higher antibacterial activity than the parent penicillins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2197570A1 true FR2197570A1 (en) | 1974-03-29 |
| FR2197570B1 FR2197570B1 (en) | 1975-10-17 |
Family
ID=9103633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7230605A Granted FR2197570A1 (en) | 1972-08-29 | 1972-08-29 | Esters of penicillins with hydroxychalcones - with higher antibacterial activity than the parent penicillins |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2341514A1 (en) |
| FR (1) | FR2197570A1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2016825A1 (en) * | 1968-07-26 | 1970-05-15 | Beecham Group Ltd | |
| FR1603296A (en) * | 1967-12-22 | 1971-03-29 |
-
1972
- 1972-08-29 FR FR7230605A patent/FR2197570A1/en active Granted
-
1973
- 1973-08-16 DE DE19732341514 patent/DE2341514A1/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1603296A (en) * | 1967-12-22 | 1971-03-29 | ||
| FR2016825A1 (en) * | 1968-07-26 | 1970-05-15 | Beecham Group Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2341514A1 (en) | 1974-03-07 |
| FR2197570B1 (en) | 1975-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |