Synthesen auf dem Phenothiazin‐Gebiet. 2. Mitteilung. N‐substituierte Mercaptophenothiazin‐Derivate

Bourquin, Jean-Pierre; Schwarb, G.; Gamboni, G.; Fischer, R.; Ruesch, L.; Guldimann, S.; Theus, V.; Schenker, E.; Renz, J.

doi:10.1002/hlca.19580410420

Cited by 43 publications

(14 citation statements)

References 21 publications

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“…The neurophysiological and biochemical mechanisms underlying the actions of the phenothiazines are poorly understood (3). The clinical and pharmacological properties of thioridazine (a phenothiazine) were investigated by Bourquin et al (4) and by Taeschler and Cerletti (5). It has an insignificant anti‐emetic and extrapyramidal syndrome‐producing action (6).…”

Section: Discussionmentioning

confidence: 99%

Thioridazine in the Management of Geriatric Patients

Ahmed¹

1968

J American Geriatrics Society

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A five‐week study of thioridazine therapy was made in 14 geriatric patients with arteriosclerotic or “senile” disorders. The initial dosage was 75 mg daily, increased by 25 mg daily at weekly intervals. Mental alertness was preserved and no side‐effects were noted, in contrast results with some of the tranquilizers previously used by the patients. Tranquilizers have an important role in the management of geriatric patients. Thioridazine seems particularly suited for use in senile agitated states, for the control of symptoms while carrying out a positive programme of rehabilitation.

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Section: Discussionmentioning

confidence: 99%

Thioridazine in the Management of Geriatric Patients

Ahmed¹

1968

J American Geriatrics Society

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“…There are only a couple of published procedures for the preparation of enantiomers of thioridazine. [30][31][32] Bourquin et al reported the first synthesis of 1, starting from racemic piperidine alcohol 5 (Scheme 1). Enantiomers of 1 were separated via chiral resolution employing di-p-tolyl-L-tartaric acid as a chiral derivatizing agent, making this a rather inefficient synthesis of the desired enantiomer.…”

Section: Letter Syn Openmentioning

confidence: 99%

Synthesis of the Enantiomers of Thioridazine

Antonsen

Monsen

Ovchinnikov

et al. 2020

SynOpen

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Thioridazine, a well-known antipsychotic drug, has shown promising effects on several bacterial strains (including Mycobacterium tuberculosis and methicillin-resistant Staphylococcus aureus). Suppressive effects towards selected cancer cell-lines have also been reported. However, due to adverse effects, the compound is no longer in use for the primary indication. More recent research has demonstrated that these side effects are limited to one of the two enantiomers, (+)-thioridazine. The question arises to whether the beneficial effects of thioridazine are limited to one enantiomer, or if (-)-thioridazine can prove itself to be useful in its pure enantiomeric state. The published procedures on the synthesis of the optically pure enantiomers of thioridazine were found to be unsatisfactory, either due to low optical purity, high cost, or problems scaling up. Herein, we have used an auxiliarybased strategy for the total synthesis of both enantiomers in high optical purity and good overall yield. The strategy can easily be scaled up. Both enantiomers were tested against several bacteria. Comparison of the racemic mixture, (-)-thioridazine and its (+)-antipode revealed that they have the same antimicrobial effects. Thus, the non-toxic enantiomer, (-)-thioridazine, can prove useful in this role and should be investigated further.

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“…A round-bottomed flask was charged with Pd-catalyst: Pd 2 (dba) 3 or Pd(OAc) 2 (5-7.5 mol%), ligand: XPhos (10-15 2-ol 12 (10), secondary amine, base: NaO t Bu or Cs 2 CO 3 , and dry toluene (5 mL). The flask was flushed with argon for 5 min.…”

Section: General Procedures For Preparation Of 1-(2-amino)-5-oxido-10hmentioning

confidence: 99%

“…6 Among the effective compounds that proved to inhibit resistance, some phenothiazine derivatives were found of high activity. 7 With some of the most important such compounds involving chloropromazine 8 , trifluoperazine 9 , thioridazine 10 , two common structural features of these compounds should be pointed out: (i) presence of an alkyl chain attached to the nitrogen atom of the phenothiazine ring; (ii) presence of an amino moiety in most of the derivatives.…”

Section: Introductionmentioning

confidence: 99%