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7-Nitroindazole

April 11, 2024

7-Nitroindazole, or 7-NI, is a heterocyclic small molecule containing an indazole ring that has been nitrated at the 7 position. Nitroindazole acts as a selective inhibitor for neuronal nitric oxide synthase, a hemoprotein enzyme that, in neuronal tissue, converts arginine to citrulline and nitric oxide (NO).[1] Nitric oxide can diffuse through the plasma membrane into neighbouring cells, allowing cell signalling, so nitroindazole indirectly inhibits this signalling process.[2][3][4] Other inhibitors exist such as 3-bromo-7-nitroindazole, which is more potent but less specific,[5] or NPA (N-propyl-L-arginine), which acts on a different site.[6]

7-Nitroindazole
Names
Preferred IUPAC name
7-Nitro-1H-indazole
Identifiers
  • 2942-42-9 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL247378 Y
ChemSpider
  • 1821 Y
ECHA InfoCard 100.019.032
  • 5127
  • 1893
UNII
  • UX0N37CMVH Y
  • DTXSID30183638
  • InChI=1S/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9) Y
    Key: PQCAUHUKTBHUSA-UHFFFAOYSA-N Y
  • InChI=1/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9)
    Key: PQCAUHUKTBHUSA-UHFFFAOYAE
  • [O-][N+](=O)c1cccc2c1[nH]nc2
Properties
C7H5N3O2
Molar mass 163.1335
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Pharmacology edit

7-Nitroindazole is under investigation as a possible protective agent against nerve damage caused by excitotoxicity or neurodegenerative diseases.[1][7] It may act by reducing oxidative stress or by decreasing the amount of peroxynitrite formed in these tissues. These effects are related to the inhibition of type 1 nitric oxide synthase. However, anticonvulsive effect is derived from some other mechanisms.[8]

See also edit

References edit

  1. ^ a b Southan GJ; Szabó C (February 1996). "Selective pharmacological inhibition of distinct nitric oxide synthase isoforms". Biochem. Pharmacol. 51 (4): 383–94. doi:10.1016/0006-2952(95)02099-3. PMID 8619882.
  2. ^ Moore PK; Wallace P; Gaffen Z; Hart SL; Babbedge RC (September 1993). "Characterization of the novel nitric oxide synthase inhibitor 7-nitro indazole and related indazoles: antinociceptive and cardiovascular effects". Br. J. Pharmacol. 110 (1): 219–24. doi:10.1111/j.1476-5381.1993.tb13795.x. PMC 2175981. PMID 7693278.
  3. ^ Babbedge RC; Bland-Ward PA; Hart SL; Moore PK (September 1993). "Inhibition of rat cerebellar nitric oxide synthase by 7-nitro indazole and related substituted indazoles". Br. J. Pharmacol. 110 (1): 225–8. doi:10.1111/j.1476-5381.1993.tb13796.x. PMC 2175991. PMID 7693279.
  4. ^ Moore PK; Babbedge RC; Wallace P; Gaffen ZA; Hart SL (February 1993). "7-Nitro indazole, an inhibitor of nitric oxide synthase, exhibits anti-nociceptive activity in the mouse without increasing blood pressure". Br. J. Pharmacol. 108 (2): 296–7. doi:10.1111/j.1476-5381.1993.tb12798.x. PMC 1907983. PMID 7680591.
  5. ^ Gammie SC; Olaghere-da Silva UB; Nelson RJ (July 2000). "3-bromo-7-nitroindazole, a neuronal nitric oxide synthase inhibitor, impairs maternal aggression and citrulline immunoreactivity in prairie voles". Brain Res. 870 (1–2): 80–6. doi:10.1016/S0006-8993(00)02404-5. PMID 10869504. S2CID 23918529.
  6. ^ Kampf C; Roomans GM (May 2001). "Effects of hypochlorite on cultured respiratory epithelial cells". Free Radic. Res. 34 (5): 499–511. doi:10.1080/10715760100300441. PMID 11378533. S2CID 5920036.
  7. ^ Schulz JB; Matthews RT; Klockgether T; Dichgans J; Beal MF (September 1997). "The role of mitochondrial dysfunction and neuronal nitric oxide in animal models of neurodegenerative diseases". Mol. Cell. Biochem. 174 (1–2): 193–7. doi:10.1023/A:1006852306789. PMID 9309687. S2CID 8301981.
  8. ^ Matsumura, N.; Kikuchi-Utsumi, K.; Nakaki, T. (2008). "Activities of 7-nitroindazole and 1-(2-(trifluoromethylphenyl)-imidazole independent of neuronal nitric-oxide synthase inhibition". J Pharmacol Exp Ther. 325 (2): 357–62. doi:10.1124/jpet.107.135160. PMID 18270316. S2CID 27063286.

External links edit


April 11, 2024
nitroindazole, heterocyclic, small, molecule, containing, indazole, ring, that, been, nitrated, position, nitroindazole, acts, selective, inhibitor, neuronal, nitric, oxide, synthase, hemoprotein, enzyme, that, neuronal, tissue, converts, arginine, citrulline,. 7 Nitroindazole or 7 NI is a heterocyclic small molecule containing an indazole ring that has been nitrated at the 7 position Nitroindazole acts as a selective inhibitor for neuronal nitric oxide synthase a hemoprotein enzyme that in neuronal tissue converts arginine to citrulline and nitric oxide NO 1 Nitric oxide can diffuse through the plasma membrane into neighbouring cells allowing cell signalling so nitroindazole indirectly inhibits this signalling process 2 3 4 Other inhibitors exist such as 3 bromo 7 nitroindazole which is more potent but less specific 5 or NPA N propyl L arginine which acts on a different site 6 7 Nitroindazole NamesPreferred IUPAC name 7 Nitro 1H indazoleIdentifiersCAS Number 2942 42 9 Y3D model JSmol Interactive imageChEMBL ChEMBL247378 YChemSpider 1821 YECHA InfoCard 100 019 032IUPHAR BPS 5127PubChem CID 1893UNII UX0N37CMVH YCompTox Dashboard EPA DTXSID30183638InChI InChI 1S C7H5N3O2 c11 10 12 6 3 1 2 5 4 8 9 7 5 6 h1 4H H 8 9 YKey PQCAUHUKTBHUSA UHFFFAOYSA N YInChI 1 C7H5N3O2 c11 10 12 6 3 1 2 5 4 8 9 7 5 6 h1 4H H 8 9 Key PQCAUHUKTBHUSA UHFFFAOYAESMILES O N O c1cccc2c1 nH nc2PropertiesChemical formula C7H5N3O2Molar mass 163 1335Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Pharmacology 2 See also 3 References 4 External linksPharmacology edit7 Nitroindazole is under investigation as a possible protective agent against nerve damage caused by excitotoxicity or neurodegenerative diseases 1 7 It may act by reducing oxidative stress or by decreasing the amount of peroxynitrite formed in these tissues These effects are related to the inhibition of type 1 nitric oxide synthase However anticonvulsive effect is derived from some other mechanisms 8 See also editDizocilpine MK 801 a non competitive antagonist of the NMDA receptor Sildenafil a drug for impotence which inhibits cGMP specific phosphodiesterase type 5 PDE5 which is responsible for degradation of cGMP which is produced by guanylate cyclase which is activated by nitric oxide produced by eNOS tetrahydrobiopterin cofactor to several enzymes including nitric oxide synthase NOS protein kinase A PKA and protein kinase C PKC References edit a b Southan GJ Szabo C February 1996 Selective pharmacological inhibition of distinct nitric oxide synthase isoforms Biochem Pharmacol 51 4 383 94 doi 10 1016 0006 2952 95 02099 3 PMID 8619882 Moore PK Wallace P Gaffen Z Hart SL Babbedge RC September 1993 Characterization of the novel nitric oxide synthase inhibitor 7 nitro indazole and related indazoles antinociceptive and cardiovascular effects Br J Pharmacol 110 1 219 24 doi 10 1111 j 1476 5381 1993 tb13795 x PMC 2175981 PMID 7693278 Babbedge RC Bland Ward PA Hart SL Moore PK September 1993 Inhibition of rat cerebellar nitric oxide synthase by 7 nitro indazole and related substituted indazoles Br J Pharmacol 110 1 225 8 doi 10 1111 j 1476 5381 1993 tb13796 x PMC 2175991 PMID 7693279 Moore PK Babbedge RC Wallace P Gaffen ZA Hart SL February 1993 7 Nitro indazole an inhibitor of nitric oxide synthase exhibits anti nociceptive activity in the mouse without increasing blood pressure Br J Pharmacol 108 2 296 7 doi 10 1111 j 1476 5381 1993 tb12798 x PMC 1907983 PMID 7680591 Gammie SC Olaghere da Silva UB Nelson RJ July 2000 3 bromo 7 nitroindazole a neuronal nitric oxide synthase inhibitor impairs maternal aggression and citrulline immunoreactivity in prairie voles Brain Res 870 1 2 80 6 doi 10 1016 S0006 8993 00 02404 5 PMID 10869504 S2CID 23918529 Kampf C Roomans GM May 2001 Effects of hypochlorite on cultured respiratory epithelial cells Free Radic Res 34 5 499 511 doi 10 1080 10715760100300441 PMID 11378533 S2CID 5920036 Schulz JB Matthews RT Klockgether T Dichgans J Beal MF September 1997 The role of mitochondrial dysfunction and neuronal nitric oxide in animal models of neurodegenerative diseases Mol Cell Biochem 174 1 2 193 7 doi 10 1023 A 1006852306789 PMID 9309687 S2CID 8301981 Matsumura N Kikuchi Utsumi K Nakaki T 2008 Activities of 7 nitroindazole and 1 2 trifluoromethylphenyl imidazole independent of neuronal nitric oxide synthase inhibition J Pharmacol Exp Ther 325 2 357 62 doi 10 1124 jpet 107 135160 PMID 18270316 S2CID 27063286 External links edit7 nitroindazole at the U S National Library of Medicine Medical Subject Headings MeSH Retrieved from https en wikipedia org w index php title 7 Nitroindazole amp oldid 1196419361, wikipedia, wiki, book, books, library,

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