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To treat diabetes. The design is an attempt to generate an analog of Idazoxan.<ref>Denis Bigg, et al. US4659731 (1987 to Synthelabo SA).</ref><ref> Fagan, Gay P.; Chapleo, Christopher B.; Lane, Anthony C.; Myers, Malcolm; Roach, Alan G.; Smith, Colin F. C.; Stillings, Michael R.; Welbourn, Anthony P. (1988). "Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists". Journal of Medicinal Chemistry. 31 (5): 944–948. doi:10.1021/jm00400a009.</ref> To treat diabetes. The design is an attempt to generate an analog of Idazoxan.<ref> Fagan, Gay P.; Chapleo, Christopher B.; Lane, Anthony C.; Myers, Malcolm; Roach, Alan G.; Smith, Colin F. C.; Stillings, Michael R.; Welbourn, Anthony P. (1988). "Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists". Journal of Medicinal Chemistry. 31 (5): 944–948. doi:10.1021/jm00400a009.</ref><ref>Denis Bigg, et al. US4659731 (1987 to Synthelabo SA).</ref>


The structure is an imidazoline and also an N-phenylindole.

According to the patent, the pharmacology is said to be α2-Receptor antagonist or α1-Receptor agonist.
==Synthesis== ==Synthesis==
Prec:<ref> Dolby, Lloyd J.; Lord, Pierre D. (1969). "2-Alkylidene-2H-indole intermediates. Thermolysis of 2-hydroxydiphenylmethylindole". The Journal of Organic Chemistry. 34 (10): 2988–2993. doi:10.1021/jo01262a042.</ref> Patent:<ref>Christopher B. Chapleo & Gay P. Fagan, US5385919 (1995 to Reckitt & Colman Products Limited).</ref> Prec:<ref> Dolby, Lloyd J.; Lord, Pierre D. (1969). "2-Alkylidene-2H-indole intermediates. Thermolysis of 2-hydroxydiphenylmethylindole". The Journal of Organic Chemistry. 34 (10): 2988–2993. doi:10.1021/jo01262a042.</ref> Patent:<ref>Christopher B. Chapleo & Gay P. Fagan, US5385919 (1995 to Reckitt & Colman Products Limited).</ref>
] ]
Ex 1: The reaction between ethyl 1-phenyl-1H-indole-2-carboxylate (1) and ethylenediamine (2) gives RX 871024 (3). Ex 1: The reaction between ethyl 1-phenyl-1H-indole-2-carboxylate (1) and ethylenediamine (2) gives RX 871024 (3).
Also, reaction of 1-phenylindole-2-carbonitrile, PC20095505 with ethylenediamine monotosylate gives higher yield. Also, reaction of 1-phenylindole-2-carbonitrile, with ethylenediamine monotosylate gives higher yield.

== References == == References ==
{{reflist}} {{reflist}}


{{Oral hypoglycemics}} {{Oral hypoglycemics}}

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Latest revision as of 00:53, 23 December 2024

RX 871024
Identifiers
IUPAC name
  • 2-(2-imidazolin-2-yl)-1-phenyl-1H-indole
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC17H15N3
Molar mass261.328 g·mol
3D model (JSmol)
SMILES
  • C1CN=C(N1)C2=CC3=CC=CC=C3N2C4=CC=CC=C4
InChI
  • InChI=1S/C17H15N3/c1-2-7-14(8-3-1)20-15-9-5-4-6-13(15)12-16(20)17-18-10-11-19-17/h1-9,12H,10-11H2,(H,18,19)
  • Key:XUIUIZMIIPNHIJ-UHFFFAOYSA-N

To treat diabetes. The design is an attempt to generate an analog of Idazoxan.

The structure is an imidazoline and also an N-phenylindole.

According to the patent, the pharmacology is said to be α2-Receptor antagonist or α1-Receptor agonist.

Synthesis

Prec: Patent:

RX 871024 synthesis
RX 871024 synthesis

Ex 1: The reaction between ethyl 1-phenyl-1H-indole-2-carboxylate (1) and ethylenediamine (2) gives RX 871024 (3). Also, reaction of 1-phenylindole-2-carbonitrile, PC20095505 with ethylenediamine monotosylate gives higher yield.

References

  1. Fagan, Gay P.; Chapleo, Christopher B.; Lane, Anthony C.; Myers, Malcolm; Roach, Alan G.; Smith, Colin F. C.; Stillings, Michael R.; Welbourn, Anthony P. (1988). "Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists". Journal of Medicinal Chemistry. 31 (5): 944–948. doi:10.1021/jm00400a009.
  2. Denis Bigg, et al. US4659731 (1987 to Synthelabo SA).
  3. Dolby, Lloyd J.; Lord, Pierre D. (1969). "2-Alkylidene-2H-indole intermediates. Thermolysis of 2-hydroxydiphenylmethylindole". The Journal of Organic Chemistry. 34 (10): 2988–2993. doi:10.1021/jo01262a042.
  4. Christopher B. Chapleo & Gay P. Fagan, US5385919 (1995 to Reckitt & Colman Products Limited).
Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)
Insulins / insulin analogs
fast-acting
short-acting
long-acting
ultra-long-acting
inhalable
  • Exubera
  • Afrezza
Non-insulins
Insulin sensitizers
Biguanides
TZDs/"glitazones" (PPAR)
Dual PPAR agonists
Amylin analogs and DACRAs
Secretagogues
KATP
Sulfonylureas
Meglitinides/"glinides"
GLP-1 receptor agonists
GLP1 poly-agonist peptides
DPP-4 inhibitors/"gliptins"
Other
Aldose reductase inhibitors
Alpha-glucosidase inhibitors
SGLT2 inhibitors/"gliflozins"
Other
Combinations


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