Polyaromatic acridine

An interesting reaction of dimsyl anion 88 is the methylation of polyaromatic compounds. Thus naphthalene, anthracene, phenanthrene, acridine, quinoline, isoquinoline and phenanthridine were regiospecifically methylated upon treatment with potassium t-butoxide and DMSO in digyme or with sodium hydride in DMSO123-125. Since ca. 50% of D was found to remain in the monomethyl derivative 93 derived from 9-deuteriophenanthrene 92, the mechanistic route shown in Scheme 2 was suggested125. 

This chapter focuses on recent developments in the design and applications of fluorescent organic markers, such as coumarins, benzoxadiazoles, acridones, acridines, polyaromatics (naphthalene, anthracene, and pyrene), fluorescein, and rho-damine derivatives, which display maximum fluorescence emission in the UV/ visible region and have been applied in the labeling of relevant biomolecules, namely DNA, RNA, proteins, peptides, and amino acids, among others. 

It is known from electrochemical studies that fullerenes are easily reduced. Up to 6 electrons can be added reversibly [19], and, as mentioned earlier, the excited states are even more easily reduced. A large number of electron donors were investigated including aromatic and alkyl amines [29,43,79,119-140,152,161], ni-troxide radicals [57,117], suspensions of Ti02 [118], polyaromatic compounds, [19,127] organo-silicon compounds, [133,158] phenothiazine, [133] acridine [145,154], (3-carotene [141], tetrathiafulvalenes [146], tetraethoxyethene [147], phthalocyanines [148], porphyrines [151,153], NADH and analogues [150,154, 155], borates [156,159], and naphtoles [23] to name a few representative cases. 

Figure 4. Heterocyclic polyaromatic TB analogs containing phenanthroline or acridine...

Mostly, electron carriers used in reduction processes are ardical anions of commercially available acceptors like nitroaromatic compounds, polyaromatic rings, aromatic heterocycles, and ketones (dinitrobenzene, benzophenones, acridine, fluorenone, diphenyl anthracene, anthracene, phenanthrene, naphthalene, and so on). Table 1 exhibits some possible mediators within a large cathodic potential range. 

Transition metal complexes of other relevant organonitrogen compounds such as isoquinoline, 5,6-benzoquinoline, 7,8-benzoquinoline, acridine, and phenanthridine are also known, and they contain theN-ligand coordinated in either the p fN) or the tl -arene fashion [49, 69, 70]. The triosmium cluster Os3(CO),o(CH3CN)2 reacts with polyaromatic N-heterocycles such as 5,6-benzoquinoline and phenanthridine in an analogous manner to Py and Q, yielding J.3, n (N,C,C) complexes [69]. 

Twenty-eight patients that required coal tar treatment on an area larger than two-thirds of the body surface were studied (Cemikova et al. 1983). Tar paste (10 and 20%) was used for treatment in one application, approximately 1-6 g of coal tar containing 0.6% acridine was spread on the patient s skin. Urine analysis was performed by TLC to obtain information on polyaromatic and heterocyclic substances excreted in the urine. Further identification of the substance was performed by GC/mass spectrometry (GC/MS). The presence of acridine in urine after the coal tar application was identified by MS. The detection of acridine in urine provided proof of the absorption of a coal tar component through the skin. However, without additional information, no statements can be made regarding the dermal absorption of other coal tar components or whether acridine was preferentially absorbed through the skin. 

Partitioning of solutes between the SCCO2 phase and the polymer phase has been studied for cross-linked PDMS and poly(cyanopropylmethylsiloxane) (PCPMS). It has ben shown that naphthalene, acridine, and 2-naphthol partition preferentially into the polymer phase, but the partition constant drops from 10 -10 below 75 bar to only 1-5 at higher pressures [35,36]. One would anticipate, therefore, that heavy polyaromatic compounds wiU be difficult to extract from liquid polymers with SCCO2. Extraction of lighter compounds is relatively facile [10]. 

---