13640-26-1

Basic information

• Product Name: pimprinine
• Synonyms: 5-(3-Indolyl)-2-Methyloxazole, WS 30581C, APHE 3;5-(1H-Indol-3-yl)-2-Methyloxazole
• CAS NO: 13640-26-1
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.224
• Mol File: 13640-26-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 213.5 °C (polymorph)
• Boiling Point: 407.8°Cat760mmHg
• Flash Point: 210°C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 1.74E-06mmHg at 25°C
• Refractive Index: 1.652
• PKA: 15.78±0.30(Predicted)
• CAS DataBase Reference: pimprinine(CAS DataBase Reference)
• NIST Chemistry Reference: pimprinine(13640-26-1)
• EPA Substance Registry System: pimprinine(13640-26-1)

Safety Data

• Hazardous Substances Data: 13640-26-1(Hazardous Substances Data)

Usage

Description

Pimprinine, an indole alkaloid derived from various Streptomyces species, is a potent inhibitor of monoamine oxidase with demonstrated anticonvulsant and analgesic properties. Its unique bioactivity and pharmacological effects make it a compound of interest for various therapeutic applications.

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

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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 articles and documents

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

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.

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-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.

Discovery of Pimprinine Alkaloids as Novel Agents against a Plant Virus

Plant viral diseases cause tremendous decreases in crop yield and quality. Natural products have always been a valuable source for lead discovery in medicinal and agricultural chemistry. A series of pimprinine alkaloids and their derivatives were prepared and identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). The antiviral activities of these alkaloids against tobacco mosaic virus (TMV) were systematically investigated for the first time. Most of the compounds exhibited higher antiviral activities than ribavirin. Compounds 5l, 9h, and 10h, which had similar or higher antiviral activities than ningnanmycin (perhaps the most widely used antiviral agent at present), emerged as new antiviral pilot compounds. This systematic structure-activity-relationship research lays the foundation for simplifying the structure of these alkaloids. The ring-open products, acylhydrazones 9a-9u, were also found to possess good antiviral activities. Moreover, all the synthesized compounds displayed broad-spectrum fungicidal activities. This study provides important information for the research and development of pimprinine alkaloids as novel antiviral agents.