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Pyrrolo[1,3]benzothiazepine-based atypical antipsychotic agents. Synthesis, structure-activity relationship, molecular modeling, and biological studies.

Overview of attention for article published in Journal of Medicinal Chemistry, January 2002
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About this Attention Score

  • Good Attention Score compared to outputs of the same age (68th percentile)
  • Good Attention Score compared to outputs of the same age and source (76th percentile)

Mentioned by

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1 Wikipedia page

Citations

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21 Dimensions

Readers on

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16 Mendeley
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Title
Pyrrolo[1,3]benzothiazepine-based atypical antipsychotic agents. Synthesis, structure-activity relationship, molecular modeling, and biological studies.
Published in
Journal of Medicinal Chemistry, January 2002
Pubmed ID
Authors

Giuseppe Campiani, Stefania Butini, Sandra Gemma, Vito Nacci, Caterina Fattorusso, Bruno Catalanotti, Gianluca Giorgi, Alfredo Cagnotto, Mara Goegan, Tiziana Mennini, Patrizia Minetti, M Assunta Di Cesare, Domenico Mastroianni, Nazzareno Scafetta, Bruno Galletti, M Antonietta Stasi, Massimo Castorina, Licia Pacifici, Orlando Ghirardi, Ornella Tinti, Paolo Carminati

Abstract

The prototypical dopamine and serotonin antagonist (+/-)-7-chloro-9-(4-methylpiperazin-1-yl)-9,10-dihydropyrrolo[2,1-b][1,3]benzothiazepine (5) was resolved into its R and S enantiomers via crystallization of the diastereomeric tartaric acid salts. Binding studies confirmed that the (R)-(-)-enantiomer is a more potent D(2) receptor antagonist than the (S)-(+)-enantiomer, with almost identical affinity at the 5-HT(2) receptor ((S)-(+)-5, log Y = 4.7; (R)-(-)-5, log Y = 7.4). These data demonstrated a significant stereoselective interaction of 5 at D(2) receptors. Furthermore, enantiomer (S)-(+)-5 (ST1460) was tested on a panel of receptors; this compound showed an intriguing binding profile characterized by high affinity for H(1) and the alpha(1) receptor, a moderate affinity for alpha(2) and D(3) receptors, and low affinity for muscarinic receptors. Pharmacological and biochemical investigation confirmed an atypical pharmacological profile for (S)-(+)-5. This atypical antipsychotic lead has low propensity to induce catalepsy in rat. It has minimal effect on serum prolactin levels, and it has been selected for further pharmacological studies. (S)-(+)-5 increases the extracellular levels of dopamine in the rat striatum after subcutaneous administration. By use of 5 as the lead compound, a novel series of potential atypical antipsychotics has been developed, some of them being characterized by a stereoselective interaction at D(2) receptors. A number of structure-activity relationships trends have been identified, and a possible explanation is advanced in order to account for the observed stereoselectivity of the enantiomer of (+/-)-5 for D(2) receptors. The molecular structure determination of the enantiomers of 5 by X-ray diffraction and molecular modeling is reported.

Mendeley readers

The data shown below were compiled from readership statistics for 16 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
United States 1 6%
Germany 1 6%
Unknown 14 88%

Demographic breakdown

Readers by professional status Count As %
Researcher 4 25%
Student > Master 4 25%
Other 3 19%
Student > Doctoral Student 2 13%
Student > Bachelor 2 13%
Other 0 0%
Unknown 1 6%
Readers by discipline Count As %
Chemistry 3 19%
Medicine and Dentistry 3 19%
Biochemistry, Genetics and Molecular Biology 3 19%
Agricultural and Biological Sciences 1 6%
Psychology 1 6%
Other 2 13%
Unknown 3 19%

Attention Score in Context

This research output has an Altmetric Attention Score of 3. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 27 November 2011.
All research outputs
#921,212
of 4,013,884 outputs
Outputs from Journal of Medicinal Chemistry
#570
of 2,953 outputs
Outputs of similar age
#40,830
of 133,894 outputs
Outputs of similar age from Journal of Medicinal Chemistry
#21
of 90 outputs
Altmetric has tracked 4,013,884 research outputs across all sources so far. This one has received more attention than most of these and is in the 63rd percentile.
So far Altmetric has tracked 2,953 research outputs from this source. They receive a mean Attention Score of 3.2. This one is in the 48th percentile – i.e., 48% of its peers scored the same or lower than it.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 133,894 tracked outputs that were published within six weeks on either side of this one in any source. This one has gotten more attention than average, scoring higher than 68% of its contemporaries.
We're also able to compare this research output to 90 others from the same source and published within six weeks on either side of this one. This one has done well, scoring higher than 76% of its contemporaries.