Phenothiazines

Gordon, Maxwell

doi:10.1016/b978-1-4832-3026-9.50010-8

Cited by 7 publications

(1 citation statement)

References 827 publications

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“…It is not known whether the central depressant and local anaesthetic properties of these drugs have a common underlying mechanism. The structural requirements for potent tranquillizing activity in the aminoalkylphenothiazine series (formula below) are well defined (Gordon, 1967…”

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confidence: 99%

On the local anaesthetic action of chlorpromazine and some non-tranquillizing analogues

Green

1970

Journal of Pharmacy and Pharmacology

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mentioning

confidence: 99%

On the local anaesthetic action of chlorpromazine and some non-tranquillizing analogues

Green

1970

Journal of Pharmacy and Pharmacology

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Alcoholation of the trifluoromethyl group. I. Ortho esters derived from 1‐ and 3‐trifluoromethylphenothiazines

Saggiomo

Asai

Schwartz

1969

Journal of Heterocyclic Chem

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The preparation of 1-trifluoromethylphenothiazine is reported. Methanolic basic hydrolysis of 1and 3-trifluoromethylphenothiazines to the corresponding ortho esters of phenothiazinecarboxylic acids is described. 2-, 3and 4-Trifluoromethylphenothiazines have re-SCHEME 1 ceived considerable attention in past years due mainly to the interest in their antioxidant properties and to the psychotropic action of their derivatives (2-9). As part of a continuing program to develop new pharmacological Hs)5J 111 agents, we required the hitherto unreported l-trifluoromethyl isomer. We now wish to report the synthesis of I II her NO2 HZN NnOll 1-trifluoromethylphenothiazine by the Smiles rearrangement (10) and the preparation of a new class of compounds, ortho esters of phenothiazinecarboxylic acids, by fluoromethylphenothiazines in methanol. Our approach to 1-trifluoromethylphenothiazine (VIII, Scheme 1) commenced with the preparation of 2-bromogood yield from 2-bromo-3-nitrobenzoic acid (I) and sulfur the basic hydrolysis [CF3 + C(OCH3),] of 1-and 3-tri-@fS% / \ ; ; ; ) I CHO V l 11(:1 JAs expected, acid hydrolysis of l-trifluoromethylphenothiazine (VIII) provided the known carboxylic acid (IX, Scheme 2). Unexpectedly, however, the reaction of VIII and methanolic potassium hydroxide produced an additional product, trimethyl orthophenothiazine-l-carboxylate (X), in 47% yield. There appears to be no previous

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Dithieno‐ and thienobenzothiazines

Grol

1974

Journal of Heterocyclic Chem

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The synthesis of some isomeric dithienothiazine systems has been described. These thiazines were made by an Ullman type cyclization reaction, starting with the appropriate dithienyl‐sulphides. During the ring closure reaction hydrogen chloride was eliminated from the β‐chloro‐propionyl side chain resulting in the formation of the acryloylthiazines 5, 7 and 11. This reaction was studied under various conditions and some of the byproducts were identified. The general applicability of the reaction was demonstrated by the synthesis of two isomeric thienobenzothiazines 14 and 16. Addition of N‐methylpiperazine afforded the (N‐methylpiperazinyl)propionylthienothiazines, which were isolated as their hydrochloride salts. The latter compounds were tested for neuroleptic and antidepressive properties, but were shown to be devoid of activity. This lack of activity is discussed in terms of the hampered formation of the radicalcations, as was shown by the electrochemical oxidation of these compounds. Efforts to reduce the carbonyl function to give the propyl chain failed, due to an elimination of the side chain.

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Phenothiazines

Cited by 7 publications

References 827 publications

On the local anaesthetic action of chlorpromazine and some non-tranquillizing analogues

On the local anaesthetic action of chlorpromazine and some non-tranquillizing analogues

Alcoholation of the trifluoromethyl group. I. Ortho esters derived from 1‐ and 3‐trifluoromethylphenothiazines

Dithieno‐ and thienobenzothiazines

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