Derivatives of benzilidine cyclohexanone, benzilidine...

Details Derivatives of benzilidine cyclohexanone, benzilidine... Derivatives of benzilidine cyclohexanone, benzilidine...

1998-02-20

2003-04-01

Padmanabhan, Sreeni (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S313000, C568S345000, C568S376000, C568S379000

Reexamination Certificate

active

06541672

ABSTRACT:

TECHNICAL FIELD OF THE INVENTION
The invention relates to benzilidine derivatives, more particular to the synthesis of benzilidine cyclohexanone, benzilidine pentanone, and benzilidine acetone, that showed pharmacological activity as bactericides, anti-oxidant, and anti-inflammation.
BACKGROUND OF THE INVENTION
The invention was initiated by the fact that curcumin with the following formula (II) was widely used for medication as anti-inflammation, anti-bacteria, antioxidant, anti-hepatotoxic, hypocholesterolaemia, anti-cyclooxygenase, anti-cancer, and radical scavanger. However, it was reported that curcumin was unstable in an alkali solution (pH >6.5).
In the mean time the use of aminophyrin as an anti-inflammatory was reported unsave as this compound could produce nitrosamine known as carcinogen. Another pyrazolone derivate (dipyron) was also known, to give adverse side effects such as agranulocytosis and allergic reaction. Similar side effects were also indicated by pyrazolone derivates (phenazone, oxyphenbutazone, phenylbutazone, etc.).
Pharmacological and toxicological profile of phenylbutazone and its derivates can be illustrated below (J. Phar. Pharmacol., 1955, 7, 1002).

Structure of pyrazolone derivates
Acut toxicity (rat),
Anti inflammation
LD 50 g/kg
activity
Intra
Substituent
(3 × 50 mg/kg)
Oral
Subcutan
peritoneal
R = n-butyl
+++
0.73
0.23
0.23
R = Y = phenyl
(Phenylbutazon)
R = allyl/propyl
+++
∞
X = Y = phenyl
R = n-butyl
+++
Toxicity
R = Y = p-
decrease
CH
3
—C
6
H
4
R = n-butyl
+
8
8
8
R = Y =
p-COOH—C
6
H
4
R = n-butyl
+
—
—
—
X = H, Y = phenyl
R = n-butyl
X = Y = (3-OH,
4 carboxy)phenyl
Cyclopentanone
On the basic the above information a research group at the faculty of Pharmacy GM focused their study using curcumin as lead compound in the order to obtain a potent anti-inflammatory agent which are more stable than curcumin and less toxic compared that of pyrazolone derivates.
SUMMARY OF THE INVENTION
Modification of the center part of curcumin using electron withdrawing as well as electron donating group gave some novel compounds as derivates of benzilidine cyclohexanone, benzilidine cyclopentanone, and benzilidine acetone. The products were proposed under the following patent names:
1. Hexagamavunone
Hexa indicates that center part of the structure is a six-member ring system, gama means Gadjah Mada, vu means Vrije Universiteit, and none indicates that the product is a ketone.
2. Pentagamavunone
Penta indicates that center part of the structure is a five-member ring system, gama means Gadjah Mada, vu means Vrije Universiteit, and none indicates that the product is a ketone.
3. Gamavutone
Gama means Gadjah mada, vu means Vrije Universiteit, and tone indicates that the product contains acetone group at the center of the molecular structure.
The process is also patented under the name of SAMTISAR meaning the process was invented by Samhoedi, Timmerman, and Sardjiman.


REFERENCES:
patent: 3389986 (1968-06-01), Bella
patent: 4552876 (1985-11-01), Jones et al.
patent: 2009504 (1971-09-01), None
Borden et al, Journal of Applied Polymer Science, 22(1), pp. 239-251 1978.*
Chem.Ind. (London), vol. 21, pp. 685-686 1970.*
N.P. Buu-Hoi et al., “Condensation product of cyclic ketones with aromatic amine aldehydes and their choleretic activity,” Chem. Abstrs., vol. 60, 10589h (1964).
E.P. Dibella, “2,6-Dibenzylidenecyclohexanones,”Chem. Abstrs., vol. 69, p. 4830 (1968).
O. Gisvold et al., “Synthesis of some &agr;,&ohgr;-bis(,4-dihydroxyphenyl)alkanes.,” Chem. Abstrs., vol. 40, 64518(1946).
B.A. Hathaway, “An aldol condensation experiment using a number of aldehydes and ketones,”J. Chem. Education, vol. 64, pp. 367-368 (Apr. 1987).
P.T. Mora et al., “Disalicylideneacetone and analogs,”Chem. Abstrs., vol. 44, 9959d (1950).
W. Rumpel, “Divanillylidenecyclohexanone,”Chem. Abstrs., vol. 49, 14802g (1995).
L.C. Raiford et al., “Condensation of 4-dimethylaminobenzalde hyde with vanillalacetone and vanillalacetone derivatives,” Chem. Abstrs., vol. 32, 74324(1938).
S. S. Sardjiman et al., “1,5-diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure-activity relationship,”Eur. J. Med. Chem., vol. 32, pp. 625-630 (1997).
H. Whitmann, “Cleavage by means of diazonium compounds and quinone imide chloride. IV. Effects alonga saturated carbon chain,”Chem. Abstrs., vol. 60, 439f, 1963.

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