2757-90-6

Basic information

• Product Name: Agaritine.
• Synonyms: Agaritine.;L-Glutamic acid 5-[2-[4-(hydroxymethyl)phenyl] hydrazide];NCI-C-08899
• CAS NO: 2757-90-6
• Molecular Formula: C₁₂H₁₇N₃O₄
• Molecular Weight: 267.283
• Mol File: 2757-90-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 207°C (rough estimate)
• Boiling Point: 410.47°C (rough estimate)
• Flash Point: 248.5°C
• Appearance: /
• Density: 1.2145 (rough estimate)
• Vapor Pressure: 2.62E-10mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• PKA: 3.4, 8.86(at 25℃)
• CAS DataBase Reference: Agaritine.(CAS DataBase Reference)
• NIST Chemistry Reference: Agaritine.(2757-90-6)
• EPA Substance Registry System: Agaritine.(2757-90-6)

Safety Data

• Hazardous Substances Data: 2757-90-6(Hazardous Substances Data)

Usage

Description

Agaritine, a compound found in mushroom species of the genus Agaricus, is known for its antiviral properties and its classification as a carcinogen. It is characterized by its colorless, glistening crystalline appearance. Agaritine and its related compounds have shown potential as inhibitors against HIV proteases, making it a subject of interest for pharmaceutical research.

Uses

Used in Pharmaceutical Industry:
Agaritine is used as an antiviral agent for its potential inhibitory effects against HIV proteases. This application is significant in the development of treatments for HIV and related viral infections.
Additionally, due to its carcinogenic properties, Agaritine may be utilized in research to better understand the mechanisms of cancer development and to potentially develop targeted therapies for specific types of cancer. However,

Air & Water Reactions

Water soluble.

Reactivity Profile

An amino acid derivative. Toxic gases are formed by mixing Agaritine. with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing Agaritine. with alkali metals.

Health Hazard

ACUTE/CHRONIC HAZARDS: Very Toxic. Hazardous decomposition products. Experimental carcinogen.

Fire Hazard

The flash point of Agaritine. has not been determined, but Agaritine. is probably combustible.

InChI:InChI=1/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1

Synthetic route

N2-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl ester) 5-(2-<4-(hydroxymethyl)phenyl>hydrazide) (71426-48-7) → β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Conditions	Yield
With hydrogen; Pd/C poisoned with quinoline-sulfur In methanol; water for 0.583333h;	82%
With hydrogen; palladium on activated charcoal

N2-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl ester) 5-(2-<4-(hydroxymethyl)phenyl>hydrazide) (71426-48-7) → β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6) + L-glutamic acid-5-<2-(4-tolyl)hydrazide>

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; water for 0.583333h; Product distribution; other catalyst (poisoned with quinoline-sulfur);

Cbz-(L)-Glu-OBn (3705-42-8) → β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) DCC / 1.) CH2Cl2, -10 deg C, 4 h; 2.) CH2Cl2, -10 deg C, 1.5 h, -10 deg C --> room temp., 1.5 h 2: 82 percent / hydrogen / 10percent Pd/C poisoned with quinoline-sulfur / methanol; H2O / 0.58 h View Scheme
Multi-step reaction with 3 steps 1: (i) Et3N, ClCO2Et, (ii) /BRN= 387378/, Et3N 2: BH3 / tetrahydrofuran 3: H2 / Pd-C View Scheme

(p-hydroxymethylphenyl)hydrazine (73454-78-1) → β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) DCC / 1.) CH2Cl2, -10 deg C, 4 h; 2.) CH2Cl2, -10 deg C, 1.5 h, -10 deg C --> room temp., 1.5 h 2: 82 percent / hydrogen / 10percent Pd/C poisoned with quinoline-sulfur / methanol; H2O / 0.58 h View Scheme

methyl 4-hydrazinobenzoate (4510-12-7) → β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / DIBAH / toluene / 0.5 h / -70 °C 2: 1.) DCC / 1.) CH2Cl2, -10 deg C, 4 h; 2.) CH2Cl2, -10 deg C, 1.5 h, -10 deg C --> room temp., 1.5 h 3: 82 percent / hydrogen / 10percent Pd/C poisoned with quinoline-sulfur / methanol; H2O / 0.58 h View Scheme

4-Hydrazinobenzoic acid (619-67-0) → β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) Et3N, ClCO2Et, (ii) /BRN= 387378/, Et3N 2: BH3 / tetrahydrofuran 3: H2 / Pd-C View Scheme

4-[N'-((S)-4-Benzyloxycarbonyl-4-benzyloxycarbonylamino-butyryl)-hydrazino]-benzoic acid (71426-47-6) → β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: BH3 / tetrahydrofuran 2: H2 / Pd-C View Scheme

β-N-(γ-L(+)-glutamyl)-4-(hydroxymethyl)phenylhydrazine (2757-90-6) + 4-t-butyl-1,2-benzoquinone (1129-21-1) → 2-amino-4-[N'-(2-tert-butyl-4,5-dihydroxy-phenyl)-N'-(4-hydroxymethyl-phenyl)-hydrazinocarbonyl]-butyric acid

Conditions	Yield
With sodium phosphate buffer; tyrosinase Mechanism; pH 6.8 disappearance;

Upstream product

• 3705-42-8 Cbz-(L)-Glu-OBn 
• 71426-47-6 4-[N'-((S)-4-Benzyloxycarbonyl-4-benzyloxycarbonylamino-butyryl)-hydrazino]-benzoic acid 
• 619-67-0 4-Hydrazinobenzoic acid 
• 4510-12-7 methyl 4-hydrazinobenzoate 
• 73454-78-1 (p-hydroxymethylphenyl)hydrazine 
• 71426-48-7 N²-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl ester) 5-(2-<4-(hydroxymethyl)phenyl>hydrazide) 

Relevant articles and documents

ISOLATION OF Β-N-(γ-GLUTAMYL)-4-FORMYLPHENYLHYDRAZINE (AGARITINAL) FROM AGARICUS CAMPESTRIS

Key Word Index-Agaricus campestris; mushrooms; aminoacid; agaritinal; β-N-(γ-glutamyl)-4-formylphenylhydrazine.The new compound, agaritinal, β-N-(γ-glutamyl)-4-formylphenylhydrazine has been isolated from Agaricus campestris.It was purified by using combination of ion-exchange and reverse phase HPLC.The structure was established by UV, MS and (1)H NMR data.

Novel Synthesis of Agaritine, a 4-Hydrazinobenzyl-Alcohol Derivative Occuring in Agaricaceae

The 4-hydrazinobenzyl alcohol (3) was prepared (58percent) by diisobutylaluminiumhydride reduction of methyl 4-hydrazinobenzoate (4), whereas LiAlH4 of LiBH4 reduction of 4 proceeded further to yield (via intermediate 3) (4-tolylhydrazine (5).The alcohol 3 was stable under O2-free conditions and exhibited no tendency to eliminate H2O, neither thermally nor with H+ catalysis.Oxidation of 3 with SeO2 yielded 4-(hydroxymethyl)benzenediazonium ion (8), identified by its azo coupling product 9 with 2-naphthol.Condensation of 3 with 1-benzyl 5-hydrogen N-(benzyloxycarbonyl)-L-glutamate (1) in presence of dicyclohexylcarbodiimide afforded 82percent of N2-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl-ester) 5-(2-hydrazide) (11) which upon controlled hydrogenolysis (quinoline-sulfur-poisoned Pd/C catalyst) gave 82percent of L-glutamic acid 5-(2-hydrazide) (1), i.e. agaritine, a metabolite of Agaricus bisporus.Without poisoning of the catalyst, hydrogenolysis of (11) yielded L-glutamic acid 5-2-(4-tolyl)hydrazide) (12).