Chemistry:Suritozole
From HandWiki
Short description: Chemical compound
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| Formula | C10H10FN3S |
| Molar mass | 223.27 g·mol−1 |
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Suritozole (MDL 26,479) is an investigational cognition enhancer. It acts as a partial inverse agonist at the benzodiazepine receptor site on the GABAA ion channel complex, but does not have either anxiogenic or convulsant effects, unlike other BZD inverse agonists such as DMCM.[1] It was investigated for the treatment of depression and Alzheimer's disease,[2] but clinical development seems to have been discontinued.
Synthesis
The reaction between monomethylhydrazine [60-34-4] (1) and methyl isothiocyanate (Trapex) [556-61-6] (2) gave 2,4-dimethylthiosemicarbazide [6621-75-6] (3). Amide formation with 3-fluorobenzoyl chloride [1711-07-5] (4) yielded 1-(3-fluorobenzoyl)-2,4-dimethylthiosemicarbazide [110623-52-4] (5). Cyclization to Suritozole (6).
See also
References
- ↑ "MDL 26,479: a potential cognition enhancer with benzodiazepine inverse agonist-like properties". Br. J. Pharmacol. 107 (1): 78–86. September 1992. doi:10.1111/j.1476-5381.1992.tb14466.x. PMID 1330168.
- ↑ "Pharmacokinetics of MDL 26479, a novel benzodiazepine inverse agonist, in normal volunteers". Biopharm Drug Dispos 18 (4): 325–34. May 1997. doi:10.1002/(SICI)1099-081X(199705)18:4<325::AID-BDD21>3.0.CO;2-1. PMID 9158880.
- ↑ Miller, JA; Dudley, MW; Kehne, JH; Sorensen, SM; Wenstrup, DL; Kane JM;. MDL 26,479 Drugs Fut 1992, 17, 1, 21.
- ↑ Kane, John M.; Dudley, Mark W.; Sorensen, Stephen M.; Miller, Francis P. (1988). "2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents". Journal of Medicinal Chemistry. 31 (6): 1253–1258. doi:10.1021/jm00401a031.
- ↑ Louks, David H.; Stolz-Dunn, Sandra K. (2007). "Kinetics for Scale-Up of a One-Pot Pathway to 5-(3-Fluorophenyl)-2,4-dihydro-2,4-dimethyl-3H-1,2,4-triazole-3-thione Using a Hybrid Model of Parallel and Consecutive Reactions". Organic Process Research & Development. 11 (5): 877–884. doi:10.1021/op700101g.
- ↑ US5856350 idem Christopher Robin Dalton, John Michael Kane, John Herr Kehne, WO patent 1996033177 (1999 to Hoechst Marion Roussel, Inc.).
- ↑ US5723624 idem Sandra K. Stolz-Dunn, David H. Louks, Yolanda M. Puga, Christian T. Goralski, WO patent 1996001812 (1998 to Merrell Pharmaceuticals Inc).
{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;
| group1 = Ionotropic | list1 = {{Navbox|subgroup | groupstyle = text-align:center | groupwidth = 5em
| group1 = GABAA | list1 =
- Agonists: (+)-Catechin
- Bamaluzole
- Barbiturates (e.g., phenobarbital)
- BL-1020
- DAVA
- Dihydromuscimol
- GABA
- Gabamide
- GABOB
- Gaboxadol (THIP)
- Homotaurine (tramiprosate, 3-APS)
- Ibotenic acid
- iso-THAZ
- iso-THIP
- Isoguvacine
- Isomuscimol
- Isonipecotic acid
- Kojic amine
- Lignans (e.g., honokiol)
- Methylglyoxal
- Monastrol
- Muscimol
- Nefiracetam
- Neuroactive steroids (e.g., allopregnanolone)
- Org 20599
- PF-6372865
- Phenibut
- Picamilon
- P4S
- Progabide
- Propofol
- Quisqualamine
- SL-75102
- TACA
- TAMP
- Terpenoids (e.g., borneol)
- Thiomuscimol
- Tolgabide
- ZAPA
- Positive modulators (abridged; see here for a full list): α-EMTBL
- Alcohols (e.g., ethanol)
- Anabolic steroids
- Avermectins (e.g., ivermectin)
- Barbiturates (e.g., phenobarbital)
- Benzodiazepines (e.g., diazepam)
- Bromide compounds (e.g., potassium bromide)
- Carbamates (e.g., meprobamate)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- Dihydroergolines (e.g., ergoloid (dihydroergotoxine))
- Etazepine
- Etifoxine
- Fenamates (e.g., mefenamic acid)
- Flavonoids (e.g., apigenin, hispidulin)
- Fluoxetine
- Flupirtine
- Imidazoles (e.g., etomidate)
- Kava constituents (e.g., kavain)<!--PMID: 9776662-->
- Lanthanum
- Loreclezole
- Monastrol
- Neuroactive steroids (e.g., allopregnanolone, [[Chemistry:Cholecholesterol]], THDOC)
- Niacin
- Nicotinamide (niacinamide)
- Nonbenzodiazepines (e.g., β-carbolines (e.g., [[abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon))
- Norfluoxetine
- Petrichloral
- Phenols (e.g., propofol)
- Phenytoin
- Piperidinediones (e.g., glutethimide)
- Propanidid
- Pyrazolopyridines (e.g., etazolate)
- Quinazolinones (e.g., methaqualone)
- Retigabine (ezogabine)
- ROD-188
- Skullcap constituents (e.g., baicalin)
- Stiripentol
- Sulfonylalkanes (e.g., sulfonmethane (sulfonal))
- Topiramate
- Valerian constituents (e.g., valerenic acid)
- Volatiles/gases (e.g., chloral hydrate, chloroform, [[Chemistry:Diethyl diethyl ether, Parparaldehyde]], sevoflurane)
- Antagonists: Bicuculline
- Coriamyrtin
- Dihydrosecurinine
- Gabazine (SR-95531)
- Hydrastine
- Hyenachin (mellitoxin)
- PHP-501
- Pitrazepin
- Securinine
- Sinomenine
- SR-42641
- SR-95103
- Thiocolchicoside
- Tutin
- Negative modulators: 1,3M1B
- 3M2B
- 11-Ketoprogesterone
- 17-Phenylandrostenol
- α5IA (LS-193,268)
- β-CCB
- β-CCE
- β-CCM
- β-CCP
- β-EMGBL
- Anabolic steroids
- Amiloride
- Anisatin
- β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
- Basmisanil
- Bemegride
- Bicyclic phosphates (TBPS, TBPO, IPTBO)
- BIDN
- Bilobalide
- Bupropion
- CHEB
- Chlorophenylsilatrane
- Cicutoxin
- Cloflubicyne
- Cyclothiazide
- DHEA
- DHEA-S
- Dieldrin
- (+)-DMBB
- DMCM
- DMPC
- EBOB
- Etbicyphat
- FG-7142 (ZK-31906)
- Fiproles (e.g., fipronil)
- Flavonoids (e.g., amentoflavone, oroxylin A)
- Flumazenil
- Fluoroquinolones (e.g., ciprofloxacin)
- Flurothyl
- Furosemide
- Golexanolone
- Iomazenil (123I)
- IPTBO
- Isopregnanolone (sepranolone)
- L-655,708
- Laudanosine
- Leptazol
- Lindane
- MaxiPost
- Morphine
- Morphine-3-glucuronide
- MRK-016
- Naloxone
- Naltrexone
- Nicardipine
- Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalutenzalutamide, Chemistry:Flutamide|flut]]amide]], nilutamide)
- Oenanthotoxin
- Pentylenetetrazol (pentetrazol)
- Phenylsilatrane
- Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
- Pregnenolone sulfate
- Propybicyphat
- PWZ-029
- Radequinil
- Ro 15-4513
- Ro 19-4603
- RO4882224
- RO4938581
- Sarmazenil
- SCS
- Suritozole
- TB-21007
- TBOB
- TBPS
- TCS-1105
- Terbequinil
- TETS
- Thujone
- U-93631
- Zinc
- ZK-93426
| group2 = GABAA-ρ | list2 =
- Agonists: BL-1020
- CACA
- CAMP
- Homohypotaurine
- GABA
- GABOB
- Ibotenic acid
- Isoguvacine
- Muscimol
- N4-Chloroacetylcytosine arabinoside
- Picamilon
- Progabide
- TACA
- TAMP
- Thiomuscimol
- Tolgabide
- Positive modulators: Allopregnanolone
- Alphaxolone
- ATHDOC
- Lanthanides
- Antagonists: (S)-2-MeGABA
- (S)-4-ACPBPA
- (S)-4-ACPCA
- 2-MeTACA
- 3-APMPA
- 4-ACPAM
- 4-GBA
- cis-3-ACPBPA
- CGP-36742 (SGS-742)
- DAVA
- Gabazine (SR-95531)
- Gaboxadol (THIP)
- I4AA
- Isonipecotic acid
- Loreclezole
- P4MPA
- P4S
- SKF-97541
- SR-95318
- SR-95813
- TPMPA
- trans-3-ACPBPA
- ZAPA
- Negative modulators: 5α-Dihydroprogesterone
- Bilobalide
- Loreclezole
- Picrotoxin (picrotin, picrotoxinin)
- Pregnanolone
- ROD-188
- THDOC
- Zinc
}}
| group2 = Metabotropic
| list2 =
| below =
- See also
- Receptor/signaling modulators
- GABAA receptor positive modulators
- GABA metabolism/transport modulators
}}
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