Pyrazolidine 3,5 Dione

1. Kristina M.K.
Kutterer et al :Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-

chlorophenyl)pyrazolidine-3,5-dione derivatives were synthesized, utilizing
microwave accelerated synthesis, for evaluation as new inhibitors of
bacterial cell wall biosynthesis. Many of them demonstrated good activity
against MurB in vitro and low MIC values against Gram-positive bacteria,
particularly penicillin-resistant Streptococcus pneumoniae (PRSP).
Derivative 7l demonstrated antibacterial activity against both Gram-positive
and Gram-negative bacteria. Derivatives 7f and 10a also demonstrated
potent nanomolar Kd values in their binding to MurB.
An efficient microwave-assisted synthesis of substituted pyrazolidinediones
was developed. These compounds showed good activity against MurB and
Gram-positive bacteria.
2. Jalal Isaad et al : Simple route to a novel class of pyrazolidine -3,5- dione

based azo dyes
We report an easiest synthesis strategy of a new class of synthetic dyes by
coupling of functionalized pyrazolidine -3,5- dione derivatives via
diazotization reaction with aromatic diamine for the azoic dyes or via
dimerization reaction to synthesize the H chromophore dyes. Electron
delocalization between the two coupled components has been studied using
UV–vis spectroscopy, infrared, and NMR spectroscopy. In addition, the
formation mechanism of such compounds has been discussed.
3. Guanghui Deng et al : Pyrazolidine -3,5- dione derivatives as potent non-

steroidal agonists of farnesoid X receptor: Virtual screening, synthesis, and
biological evaluation
The identification of a novel pyrazolidine -3,5- dione based scaffold
hit compound as Farnesoid X receptor (FXR) partial or full agonist has been
accomplished by means of virtual screening techniques. A series of
pyrazolidine -3,5- dione derivatives (1a–u and 7) was designed,
synthesized, and evaluated by a cell-based luciferase transactivation assay
for their agonistic activities against FXR. Most of them showed agonistic
potencies and 10 of them (1a, 1b, 1d–f, 1j, 1n, 1t, 5b, and 7) exhibited
lower EC50 values than the reference drug CDCA. Molecular modeling
studies for the representative compounds 1a, 1d, 1f, 1j, 1n, 1u, 5b, and 7
were also presented. The novel structural scaffold has provided a new
direction for finding potent and selective FXR partial and full agonists
(referred to as ‘selective bile acid receptor modulators’, SBARMs).
A series of novel non-steroidal compounds as FXR agonists and
partial agonists was discovered by means of virtual screen and chemical
synthesis.
4. Kristina M.K. Kutterer et al : 4-Alkyl and 4,4′-dialkyl 1,2-bis(4-

chlorophenyl)pyrazolidine -3,5- dione derivatives as new inhibitors of
bacterial cell wall biosynthesis
Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-chlorophenyl) pyrazolidine -
3,5- dione derivatives were synthesized, utilizing microwave accelerated
synthesis, for evaluation as new inhibitors of bacterial cell wall biosynthesis.
Many of them demonstrated good activity against MurB in vitro and low MIC
values against Gram-positive bacteria, particularly penicillin-resistant
Streptococcus pneumoniae (PRSP). Derivative 7l demonstrated antibacterial
activity against both Gram-positive and Gram-negative bacteria. Derivatives 7f
and 10a also demonstrated potent nanomolar Kd values in their binding to
MurB.
An efficient microwave-assisted synthesis of substituted
pyrazolidinediones was developed. These compounds showed good activity
against MurB and Gram-positive bacteria.
5. I.G. Voigt-Martin et al : The use of maximum entropy and likelihood

ranking to determine the crystal structure of 4-(4′-(N,N-
dimethyl)aminobenzylidene)-pyrazolidine -3,5- dione at 1.4 Å resolution
from electron diffraction and high-resolution electron microscopy image
data
The potential maps obtained by applying the method of combined
entropy maximisation and likelihood ranking to electron diffraction data are
compared with the results obtained from high-resolution electron
microscopy and molecular modelling for the non-linear optical material 4-
(4′-(N,N-dimethyl)aminobenzylidene)- pyrazolidine -3,5- dione,
C12H13N3O2. An excellent agreement has been obtained. This reinforces
claims that the maximum entropy (ME) method is a reliable means of
structure determination from electron diffraction data, and hence of
ascertaining the suitability of organic molecules for second harmonic
generation (SHG).
6. Kyung Ah Koo et al : Christine Herrenknecht :Dependence of the retention

of pyrazolidine -3,5- diones on eluent pH in reversed-phase high-
performance liquid chromatography
.QSAR analysis of pyrazolidine -3,5- diones derivatives as Dyrk1A inhibitors
Individuals with Down syndrome (DS) suffer from mental retardation.
Overexpression and the resulting increased specific activity of Dyrk1A
kinase located on chromosome 21 cause a learning and memory deficit in
Dyrk1A transgenic mice. To search for therapeutic agents with Dyrk1A
inhibition activity, previously we obtained HCD160 as a new hit compound
for Dyrk1A inhibition. In the present study, we synthesized 34 HCD160
derivatives to investigate the quantitative structure–activity relationship
(QSAR). This analysis could provide important information for novel drug
discovery for treatment of DS related learning and memory deficits.
The QSAR analysis of 34 pyrazolidine -3,5- diones derivatives of
HCD160 showed that the presence of the 3 -nitro-4-hydroxyphenyl moiety
enhanced the inhibition activity for Dyrk1A.
7. Md.Taifur Rahman et al : Synthesis of 4,4-bis(2-
hydroperoxyalkyl)pyrazolidine -3,5- diones using manganese(III)-catalyzed
autoxidation
The autoxidation of a mixture of 1,2-disubstituted pyrazolidine -3,5- diones 1 and
alkenes 2 in the presence of a catalytic amount of manganese(III) acetate
dihydrate in air gave 4,4-bis(2-hydroperoxyalkyl) pyrazolidine -3,5- diones 3 in
75–96% yields. The structure of the bis(2-hydroperoxyethyl) pyrazolidine -3,5-
dione 3 (R1=R2=Ph, R 3 =R4=4-FC6H4) has been corroborated by an X-ray single
crystallographic analysis. On the other hand, the manganese(III) acetate
oxidation of a mixture of 1 (R1=R2=Ph) and 2 (R 3 =R4=Ph) at elevated
temperature gave 4,4-bis(2,2-diphenylethenyl)-1,2-diphenylpyrazolidine-3,5-
dione (4) in good yield.
Graphic
8. Md. Taifur Rahman et al : Manganese(III)-based oxidation of 1,2-
disubstituted pyrazolidine -3,5- diones in the presence of alkenes
The manganese(III)-catalyzed aerobic oxidation of 1,2-disubstituted
pyrazolidine -3,5- diones 1 in the presence of alkenes 2 gave the corresponding
pyrazolidinediones 3 which were doubly hydroperoxyalkylated at the 4-position
in high yields. On the other hand, pyrazolidinediones 1 were oxidized with
manganese(III) acetate in the presence of alkenes 2 at elevated temperature to
produce the 4,4-bis(alkenyl)pyrazolidinediones 4 in good yields instead of the
pyrazolidine -fused dihydrofuran analogue IV. A similar cerium(IV)-mediated
oxidation of pyrazolidinedione 1a with an alkene 2a afforded the doubly 4-
methoxyethylated derivative 5. The stability of the free hydroperoxyl group and
the reaction pathway for the aerobic and the metal-mediated oxidation reactions
were also discussed.
9. Yigang He et al : A photoprecursor for difluorocarbene
4,4-Difluoropyrazolidine-3,5-dione was synthesized as a precursor for the
corresponding pyrazolinedione, envisioned as a photochemical source of
difluorocarbene. However, this azo compound proved to be far too unstable. In
contrast, 10,10-difluorobicyclo[4.3.1]deca-1,3,5-triene, readily synthesized
from indane, was found to be a practical source of difluorocarbene for
photochemical as well as thermal cyclopropanation reactions.
10. Michel Muehlebach et al : Aryldiones incorporating a

[1,4,5]oxadiazepane ring. Part I: Discovery of the novel cereal herbicide
pinoxaden. Derivatives of the new class of 3 -hydroxy-4-phenyl- 5 -oxo-
pyrazolines were optimized towards both herbicidal activity on key annual
grass weed species and selectivity in small grain cereal crops. The generic
structure can be separated into three parts for the analysis of the structure–
activity relationships, namely the aryl, the dione with its prodrug forms and the
hydrazine moiety. Each area appears to play distinct and different roles in
overall expression of biological performance which is further beneficially
influenced by adjuvant response and safener action. Pinoxaden 6, a novel
graminicide for use in wheat and barley incorporating a [1,4,5]oxadiazepane
ring, eventually emerged as a development candidate from the discovery and
optimization process.
11. M.F. Kasper et al : Defined test reagents for the diagnosis of drug-induced
allergy: Antibody-dependent skin reactions towards pyrazolinone and
pyrazolidinedione derivatives in the guinea pig
Chemically defined haptenic reagents and haptenic conjugates were

synthesized for use in clinical skin testing. One series of reagents was based
on the 1-phenyl-2,3-dimethyl-3 -pyrazolin- 5 -one structure, a second series
on 1,2-diphenylpyrazolidine -3,5- dione. Haptens were connected via
flexible spacer molecules which insert considerable distances between
haptenic moieties and carriers. The skin test reagents were hexavalent
conjugates prepared from the bis-penta-L-lysine carrier ‘PAL’. The
methodological details exemplify the application of N-hydroxysuccinimide
activated ester derivatives for the preparation of peptidic conjugates. Rabbit
and guinea-pig antisera against the haptens were obtained by immunization
with human serum albumin conjugates. Efficacy and cross-reactivity
relationshios were assessed by guinea pig PCA and by testing actively
immunized guinea pigs. A striking lack of cross-reactivity was found
between pyrazolinone and pyrazolidinedione haptenic reagents in all test
systems. On the other hand, the elicitation of homologous anaphylaxis was
highly effective with the PAL conjugates. The data presented and discussed
provide a basis for the evaluation of clinical tests performed in order to
define drug-induced allergic reactions. They are relevant for immediate-type
skin reactions as well as for serological methods.

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1. Kristina M.K.

Kutterer et al :Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-

2. Jalal Isaad et al : Simple route to a novel class of pyrazolidine -3,5- dione

3. Guanghui Deng et al : Pyrazolidine -3,5- dione derivatives as potent non-

4. Kristina M.K. Kutterer et al : 4-Alkyl and 4,4′-dialkyl 1,2-bis(4-

5. I.G. Voigt-Martin et al : The use of maximum entropy and likelihood

6. Kyung Ah Koo et al : Christine Herrenknecht :Dependence of the retention

10. Michel Muehlebach et al : Aryldiones incorporating a

Chemically defined haptenic reagents and haptenic conjugates were

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