13640-26-1

Usage

Uses

Used in Pharmaceutical Applications:
Pimprinine is used as an inhibitor of monoamine oxidase for its ability to regulate the levels of monoamines in the brain, which are associated with mood, anxiety, and other neurological conditions.
Used in Anticonvulsant Applications:
Pimprinine is used as an anticonvulsant agent for its promising activity in electric seizure threshold tests in mice, comparable to phenylhydantoin, making it a potential candidate for the treatment of seizure disorders.
Used in Tremor Treatment:
Pimprinine is used as an anti-tremor agent for its demonstrated ability to inhibit tremorine-induced tremors in mice, suggesting its potential use in treating conditions characterized by involuntary muscle movements.
Used in Analgesia:
Pimprinine is used as an analgesic agent for its ability to provide pain relief in mice, indicating its potential application in the management of pain associated with various conditions.

InChI:InChI=1/C12H10N2O/c1-8-13-7-12(15-8)10-6-14-11-5-3-2-4-9(10)11/h2-7,14H,1H3

Upstream product

• 1016-47-3 N-Acetyltryptamine 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 98258-82-3 3-(2-aminoacetyl)-1-methoxyindole 
• 98258-81-2 3-(2-chloroacetyl)-1-methoxyindole 
• 703-80-0 3-acetylindole 
• 302-72-7 rac-Ala-OH 
• 61364-28-1 methyl 5-(1H-indol-3-yl)-2-methyloxazole-4-carboxylate 
• 120-72-9 indole 
• 98258-84-5 5-(1-methoxyindol-3-yl)-2-methyloxazole 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 7269-72-9 3-indolylglyoxal 
• 952527-75-2 1-tosyl-3-((trimethylsilyl)ethynyl)-1H-indole 
• 170456-80-1 3-iodo-1-tosyl-1-indole 
• 61-54-1 tryptamine 

Related news

Original articleSynthesis and fungicidal activity of novel pimprinine (cas 13640-26-1) analogues09/05/2019

A simple and efficient synthetic protocol for 5-(3-indolyl)-oxazoles has been developed and further used to synthesize a series of novel analogues of natural product pimprinine. All new compounds were identified by 1H NMR, high resolution mass spectrometry, and the structures of 10 and 18o were ...detailed

Relevant academic research and scientific papers

A facile synthesis of naturally occurring 5-(3-indolyl)oxazoles

A simple and efficient synthesis of naturally occurring 5-(3-indolyl)oxazoles is described. The key steps of this convergent approach are the formation of a 3-tosyloxyacetyl-1-benzenesulfonylindole, a 3-amino-acetyl-1-benzenesulfonylindole hydrochloride a

One-pot total synthesis: The first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners from amino acids

In this work, we accomplished the first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners: pimprinine, pimprinethine, pimprinaphine, WS-30581A, WS-30581B, laboradorin 1, uguenenazole, balsoxine, texamine in one-pot from commercially available starting materials including amino acids. Further investigating into the mechanism revealed that this improved transformation was achieved by the integration of iodination, Kornblum oxidation, condensation, decarboxylation, annulation, and oxidation reaction sequence.

Synthesis of oxazolylindolyl alkaloids via rhodium carbenoids

The oxazolylindole alkaloids pimprinine (1a), pimprinethine (1b) and WS-30581 A (1c) are readily obtained in two steps by rhodium(II) catalysed reaction of N-Boc-3-diazoacetylindole with the appropriate nitrile followed by removal of the Boc-group.

First reported propylphosphonic anhydride (T3P) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles

In the present work, a propylphosphonic anhydride (T3P) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitri

Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: An approach to the synthesis of pimprinine

An efficient and straightforward method for the production of 5-(3-indolyl)azoles incorporating the privileged structures indoles and azoles via palladium-catalyzed double C-H bond cleavage under mild conditions was disclosed. As expected, this protocol provided an easy method for the synthesis of indole alkaloids pimprinine and WS-30581 A in moderate yields. This journal is

Natural product Pimprinine derivative as well as preparation method and application thereof

The invention discloses a Pimprinine derivative as shown in a formula III in the description. The invention also discloses a preparation method of the Pimprinine derivative, and a series of Pimprinine derivatives are synthesized by taking Pimprinine as a lead, combining the structural characteristics of Pimprinine, taking cheap and easily available indole as a raw material, modifying and transforming different sites of a framework structure of the indole and introducing different substituent groups. The Pimprinine derivative disclosed by the invention has good bactericidal activity, shows efficient and/or broad-spectrum bactericidal activity, and can be applied to crop diseases caused by fungi, bacteria and viruses.

Indole heterocyclic compound, preparation method thereof and application of indole heterocyclic compound in prevention and treatment of plant diseases

The invention discloses an indole heterocyclic compound as well as a preparation method and application thereof in prevention and treatment of plant diseases. According to the method, indole is reacted with oxalyl chloride to obtain indole oxalyl chloride, then indole oxalyl chloride is reduced by tributylstannane to obtain indole carbonyl acetaldehyde, and finally indole carbonyl acetaldehyde isreacted with a corresponding amino acid under the catalysis of iodine to obtain a compound. The indole heterocyclic compound provided by the invention shows especially excellent plant virus resistingactivity, can well inhibit the tobacco mosaic virus, and also shows broad-spectrum plant pathogenic bacteria resisting activity.

Indole-based heterocyclic compound as well as preparation method and application thereof in prevention and treatment of plant diseases

The invention discloses an indole-based heterocyclic compound as well as a preparation method and application thereof in prevention and treatment of plant diseases. According to the method, indole isreacted with oxalyl chloride to obtain indole oxalyl chloride, then indole oxalyl chloride is reduced by tributylstannane to obtain indole carbonyl acetaldehyde, and finally indole carbonyl acetaldehyde is reacted with a corresponding amino acid under the catalysis of iodine to obtain a compound; or indole hydrazide is reacted with an aldehyde, and oxidizing with iodobenzene acetate is carried outto obtain the compound. The indole heterocyclic compound provided by the invention shows especially excellent plant virus resisting activity, can well inhibit the tobacco mosaic virus, and also showsbroad-spectrum plant pathogenic bacteria resisting activity.

Hydrogen Isotope Exchange Catalyzed by Ru Nanocatalysts: Labelling of Complex Molecules Containing N-Heterocycles and Reaction Mechanism Insights

Ruthenium nanocatalysis can provide effective deuteration and tritiation of oxazole, imidazole, triazole and carbazole substructures in complex molecules using D2 or T2 gas as isotopic sources. Depending on the substructure considere

Synthesis of 1-methoxyindoles and related analogs of pimprinine, (±)-chelonin A and B, based on 1-hydroxy-indole chemistry

The total synthesis of pimprinine, (±)-chelonin A and B, and their analogs are achieved based on 1-hydroxyindole chemistry.