The DOI matches its Crossref record; 18 of the 18 references it cites were found in a registry or an index.
Structure−Activity Relationships of Pyrazole Derivatives as Cannabinoid Receptor Antagonists
Open accessAbstract
As a potent, specific antagonist for the brain cannabinoid receptor (CB1), the biarylpyrazole N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2, 4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A; 1) was the lead compound for initiating studies designed to examine the structure-activity relationships of related compounds and to search for more selective and potent cannabimimetic ligands. A series of pyrazole derivatives was designed and synthesized to aid in the characterization of the cannabinoid receptor binding sites and also to serve as potentially useful pharmacological probes. Therapeutically, such compounds may have the ability to antagonize harmful side effects of cannabinoids and cannabimimetic agents. Structural requirements for potent and selective brain cannabinoid CB1 receptor antagonistic activity included (a) a para-substituted phenyl ring at the 5-position, (b) a carboxamido group at the 3-position, and (c) a 2,4-dichlorophenyl substituent at the 1-position of the pyrazole ring. The most potent compound of this series contained a p-iodophenyl group at the 5-position, a piperidinyl carboxamide at the 3-position, and a 2,4-dichlorophenyl group at the 1-position of the pyrazole ring. The iodinated nature of this compound offers additional utility as a gamma-enriching SPECT (single photon emission computed tomography) ligand that may be useful in characterizing brain CB1 receptor binding in vivo.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Isolation and Structure of a Brain Constituent That Binds to the Cannabinoid Receptor
Devane, W. A., Hanuš, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., & Mechoulam, R. (1992) · Science · doi:10.1126/science.1470919 · Cited by 5,633
Self-citationMolecular characterization of a peripheral receptor for cannabinoids
Munro, S., Thomas, K. L., & Abu-Shaar, M. (1993) · Nature · doi:10.1038/365061a0 · Cited by 5,092
SR141716A, a potent and selective antagonist of the brain cannabinoid receptor
Rinaldi-Carmona, M., Barth, F., Héaulme, M., Shire, D., Calandra, B., Congy, C., Martinez, S., Maruani, J., Néliat, G., Caput, D., et al. (1994) · FEBS Letters · doi:10.1016/0014-5793(94)00773-x · Cited by 1,757
Pasternack, B. S., & Colquhoun, D. (1972) · Journal of the American Statistical Association · doi:10.2307/2284489 · Cited by 547
pA2 and receptor differentiation: A statistical analysis of competitive antagonism
Tallarida, R. J., Cowan, A., & Adler, M. W. (1979) · Life Sciences · doi:10.1016/0024-3205(79)90505-8 · Cited by 405
Sharp, D., Blinderman, L., Combs, K. A., Kienzle, B., Ricci, B., Wager-Smith, K., Gil, C. M., Turck, C. W., Boumas, M.-E., Rader, D. J., et al. (1993) · Nature · doi:10.1038/365065a0 · Cited by 393
(R)-Methanandamide: A Chiral Novel Anandamide Possessing Higher Potency and Metabolic Stability
Abadji, V., Lin, S., Taha, G., Griffin, G., Stevenson, L. A., Pertwee, R. G., & Makriyannis, A. (1994) · Journal of Medicinal Chemistry · doi:10.1021/jm00038a020 · Cited by 346
Self-citationCannabinoids as Therapeutic Agents
(2019) · Chapman & Hall/CRC eBooks · doi:10.1201/9780429260667 · Cited by 311
Rinaldi-Carmona, M., Barth, F., Héaulme, M., Alonso, R., Shire, D., Congy, C., Soubrié, P., Brelière, J.-C., & Le Fur, G. (1995) · Life Sciences · doi:10.1016/0024-3205(95)00174-5 · Cited by 303
The central neuropharmcology of psychotropic cannabinoids
Pertwee, R. G. (1988) · Pharmacology & Therapeutics · doi:10.1016/0163-7258(88)90106-4 · Cited by 178
Self-citation
Cited by
International Union of Pharmacology. XXVII. Classification of Cannabinoid Receptors
Howlett, A. C., Barth, F., Bonner, T. I., Cabral, G., Casellas, P., Devane, W. A., Felder, C. C., Herkenham, M., Mackie, K., Martin, B. R., et al. (2002) · Pharmacological Reviews · doi:10.1124/pr.54.2.161 · Cited by 2,819
Self-citationThe Endocannabinoid System as an Emerging Target of Pharmacotherapy
Pacher, P., Bátkai, S., & Kunos, G. (2006) · Pharmacological Reviews · doi:10.1124/pr.58.3.2 · Cited by 2,077
From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles
Fustero, S., Sánchez-Roselló, M., Barrio, P., & Simón-Fuentes, A. (2011) · Chemical Reviews · doi:10.1021/cr2000459 · Cited by 1,155
Ramírez, B. G., Blázquez, C., del Pulgar, T. G., Guzmán, M., & de Ceballos, M. L. (2005) · The Journal of Neuroscience · doi:10.1523/jneurosci.4540-04.2005 · Cited by 785
Ibrahim, M. M., Deng, H., Zvonok, A., Cockayne, D. A., Kwan, J., Mata, H. P., Vanderah, T. W., Lai, J., Porreca, F., Makriyannis, A., et al. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1834309100 · Cited by 491
Self-citation
Metadata
- Authors
- Lan, R., Liu, Q., Fan, P., Lin, S., Fernando, S. R., McCallion, D., Pertwee, R., & Makriyannis, A.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-02-01
- Volume
- 42
- Issue
- 4
- Pages
- 769-776
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2061601726
- Cited by
- 447
- References
- 18
- FWCI
- 4.44
- Type
- journal article
- Language
- en
- Open access
- green
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
How to cite
Cite CoChat for the checks on this page, and the paper for its own findings.
- This page
- CoChat. (2026). Citation check: Structure−Activity Relationships of Pyrazole Derivatives as Cannabinoid Receptor Antagonists. https://app.cochat.ai/papers/10.1021/jm980363y
- The paper
- Lan, R., Liu, Q., Fan, P., Lin, S., Fernando, S. R., McCallion, D., Pertwee, R., & Makriyannis, A. (1999). Structure−Activity Relationships of Pyrazole Derivatives as Cannabinoid Receptor Antagonists. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm980363y
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
