Coumarins chemical structure

Fig. 6.4. Chemical structures of coumarin and some of its fluorescent derivatives.

SCHEME 3.40 Chemical structures of green dopants of Coumarin dyes. 

The comparison of three coumarin compounds, 4-(bromomethyl)-7-methoxy-coumarin (Br-MMC), 7-(diethylamino)coumarin-3-carbohydrazide (DCCH), and 7-(diethylamino)-3-[(4-(iodoacetyl)amino)phenyl]-4-methylcoumarin(DCIA) as potential chemiluminescence with HPLC was reported by Grayeshi and Vasto (35) (see Chemical Structure 2). 

Fig. 7 Chemical structures and calculated logP values of 3-formylchromone and coumarin derivatives (FC1-16)...

Scheme 8-1. Chemical structures of naturally occurring Calophyllum coumarins.

Optical brighteners are usually derivatives of coumarin, stilbene, dis-tyrylbipheny, and bis(benzoxazole). Examples of chemical structures of some important optical brighteners are given ... 

Chemical Structure Psoralens are planar, tricyclic compounds, consisting of a furan ring fused to a coumarin moiety... 

Chart 1.16 Chemical structures of a poly(2,5-dialkoxy-p-phenylene ethynylene), PPE, and 7-diethylamino-4-methyl-coumarin, DMC. 

The Laboratory of Lactones, Coumarins, and Terpenoids (headed by Prof. G.P Sidyakin) studied various plants for lactone content, particularly for the lactones leucomisine and austricine, which were isolated from Artemisia leucodes. Both lactones possess pronounced anti-inflammatory action. As a compound possessing pronounced angio-protective, hypolipidemic, hypo-cholesterolemic, and anti-inflammatory actions, leucomisine has passed medical tests and has been introduced into medical practice under the preparation name Oligvon. Since 1970, systematic studies of chemical compounds found in various species of the genus Ferula, which grows in the territory of Uzbekistan and adjacent republics, have been conducted. As a result, more than 50 species of Ferula have been investigated, from which more than 250 new terpenoids, coumarins, and esters have been isolated and their chemical structures determined. Natural esters of mono- and sesquiterpene alcohols with aromatic acids were discovered for the first time in this lab (Kurmukov and Akhmedkhodzhaeva 1994). 

The contradictory observations on the toxicity of coumarin stimulated our research into closely related coumarin derivatives in biochemical-pharmacological studies. Considering the limited information available in the various reviews on the biological properties of these compounds, the main emphasis in this paper will be placed on this aspect. It has been considered important to discuss the chemical structure-biological activity relationship of simple coumarins, coumarin anticoagulants, light sensitisers, aflatoxins, and related isocoumarin... 

The relationship between the chemical structure and toxicity of various coumarin insecticides and anthelmintics are compiled (Table 3.13), and for comparison, some other related compounds are also tabulated. The mammalian toxicity of these compounds is moderate, and their selective action on insects is coimected with differences in metabolism. In mammals these chemicals are probably rapidly metabolised by hydrolysis between the aromatic and phosphate groups, whereas in insects by slow oxidation of the phosphorothionate to phos-... 

Other Names Coumarin 1,2-Benzopyrone 2-Propenoic acid, 3-(2-hydroxyphenyl)-, 8-lactone 5,6-Benzo-2-pyrone Benzo-a-pyrone Coumarinic anhydride NSC 8774 Rattex Tonka bean camphor cis-o-Coumarinic acid lactone o-Hydroxycinnamic acid lactone CA Index Name 2H-l-Benzopyran-2-one CAS Registry Number 91-64-5 Merck Index Number 2562 Chemical Structure... 

Other Names Coumarin, 6,7-dihydroxy- Esculetin 6,7-Dihydroxy-2-benzopyrone 6,7-Dihydroxycoumarin Aesculetin Asculetine Cichorigenin Cichoriin aglycon Esculetol Esculin aglycon NSC 26428 Esculetin CA Index Name 2H-l-Benzopyran-2-one, 6,7-dihydroxy-CAS Registry Number 305-01-1 Merck Index Number 3697 Chemical Structure... 

Other Names Coumarin, 7-hydroxy-4-methyl- Umbelliferone, 4-methyl- P-Methylumbelliferone 4-MU 4-Methyl-7-hydroxycoumarin 4-MethylumbelUferone 7-Hydroxy-4-methyl-2-chrome-none 7-Hydroxy-4-methyl-2-oxo-3-chromene 7-Hydroxy-4-methyl-2H-l-benzopyran-2-one 7-Hydroxy-4-methyl-2H-chromen-2-one 7-Hydroxy-4-melhylcoumarin BilcoUc Bilicante Bili-ton H Cantabilin Cantabiline Cholestil Cholonerton Cholspasmin Coumarin 4 Coumarin 456 Cumarote C Eurogale Himecol Hymecromone Imecromone LM 94 Medilla Mendiaxon NSC 19026 NSC 9408 Omega 127 Pilot 447 CA Index Name 2H-l-Benzopyran-2-one, 7-hydroxy-4-methyl-CAS Registry Number 90-33-5 Merck Index Number 4854 Chemical Structure... 

The basic skeleton of isoprenoids may be modified by the introduction of a wide variety of chemical groups, by isomerization, shift of double bonds, methyl groups, etc. Hence a bewildering number of chemical structures arises. In addition compounds derived from other biogenic pathways may contain isoprene residues. For instance the K vitamins (D 8.1), ubiquinones (D 8.3), chlorophylls (D 10.1), plastoquinones, and tocopherylquinones (D 22.4) have isoprenoid side chains with up to ten isoprene units. Polyketides (D 3.3), alkaloids (D 8.4.2), and coumarins (D 22.2.2) may be substituted by dimethylallyl groups. The terpene residues are attached to nucleophilic sites, such as active methylene groups and phenolic oxygen atoms. 

Perkin s later years were as productive as his earlier ventures. He developed methods for the preparation of aminoacetic add. He established the stmctural relationships between tartaric, fumaric, and maleic adds, and synthesized dn-namic acid. This last endeavor led to the development of what is now known as the Perkin reaction.The reaction is widely used to prepare unsaturated adds from aromatic aldehydes. These studies led to his synthesis of coumarin (actually it was the first condensation product he obtained with the dassic reaction see also www)-t> Experiment [3Aadv])- Other areas investigated by Perkin dealt with the relationship of physical properties and chemical structure. 

The organic dyes used for lasers can be classified on the basis of molecular structure terphe-nyls (spectral range 312-400 nm) coumarines (420 - 580nm) rhodamines (570-720 nm), oxa-zines (680-860 nm). Each class consists of several dyes with slightly modified chemical structure and, hence, slightly shifted absorption and luminescence bands. There are special dyes for UV and near IR. 

Moreover, according to chemical structure, polyphenols can be divided in classes as simple phenols, benzoquinones, phenolic acids, acetophenones, phenylacetic acids, hrodroxycinnamic acids, phenylpropenes, coumarins, isocoumarins, chromones, naphthoquinones, xanthones, stilbenes, anthraquinones, lignans, neolignans, lignins, and flavonoids. The latter allow to consider 13 subclasses with more than 5,000 compounds (Fig. 74.2). 

Fig. 1.1 Basic chemical structures of different types of coumarins...

FIGURE 22-1. Chemical structure of (A) 4-hydroxy-coumarin and IB) indane 1,3-dlone. 

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