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Berenil

Berenil structure

CAS No:
908-54-3
Formula:
C14H15N7.2C4H7NO3
Chemical Name:
Berenil
Synonyms:
Glycine,N-acetyl-,compd. with 4,4′-(1-triazene-1,3-diyl)bis[benzenecarboximidamide] (2:1);Glycine,N-acetyl-,compd. with 4,4′-(diazoamino)dibenzamidine (2:1);Glycine,N-acetyl-,compd. with 4,4′-(azoamino)dibenzamidine;Benzamidine,4,4′-diazoaminodi-,diaceturate;Benzamidine,4,4′-(diazoamino)di-,compd. with N-acetylglycine (1:2);Benzenecarboximidamide,4,4′-(1-triazene-1,3-diyl)bis-,compd. with N-acetylglycine (1:2);Azidin;Azidine;Di-(4-amidinophenyl)-triazine-(N-1,3)-diaceturate;Berenil;Diminazene diaceturate;Diminazene aceturate;Diminazine aceturate;4,4′-Diamidinodiazoaminobenzene diaceturate;4,4′-(Diazoamino)dibenzamidine diaceturate;1,3-Bis(p-amidinophenyl)triazene bis(N-acetylglycinate);1,3-Bis[4-guanylphenyl]triazene diaceturate;p,p′-Diguanyldiazoaminobenzene diaceturate;Ganasag;Ganaseg;Beronal;Diaminazene aceturate;Veriben;Diminazine diaceturate;Diminasan;Fatrybanil;Tricip Plus;Neozidin-M;859758-13-7
Categories:
Organic Chemistry > Triazenes

Description

Diminazene aceturate (Diminazene diaceturate) is an anti-trypanosome agent for livestock. The main biochemical mechanism of the trypanocidal actions of Diminazene aceturate is by binding to trypanosomal kinetoplast DNA (kDNA) in a non-intercalative manner through specific interaction with sites rich in adenine-thymine base pairs. Diminazene aceturate is also an angiotensin-converting enzyme 2 (ACE2) activator and has strong and potent anti-inflammatory properties[1][2][3].

Berenil Basic Attributes

Molecular Weight：

515.52

Exact Mass：

515.22400

EC Number：

212-999-2

UNII：

M011GS5PF5

NSC Number：

759843|114835

Characteristics

PSA：

269

XLogP3：

3.23460

Appearance：

solid

Melting Point：

202 °C

Boiling Point：

463.3°C at 760 mmHg

Flash Point：

234ºC

Storage Conditions：

0-6°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

MB7605000

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P322, P330, P337+P313, P363, P403+P233, P405, P501

Hazard Statements：

H302

Drug Information

MeSH：

Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA. (See all compounds classified as Intercalating Agents.)|Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)|Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal Agents.)

MeSH Entry Terms：

1,3-bis(4'-amidinophenyl)triazene N-acetylglycine

Berenil Use and Manufacturing

Methods of Manufacturing

Using p-nitrobenzoic acid as the raw material, it will react with p-toluenesulfonamide at high temperature to form p-nitrobenzonitrile (C7H4N2O2[619-72-7]. Then it is added and aminated by p-nitrobenzonitrile , Reduction, diazotization, coupling, and salt formation to get diamidine. 1. Addition, amination Add p-nitrobenzonitrile, methanol, sodium methoxide to the reaction pot, stir to dissolve, and react at 25-30℃ for 3h .Add ammonium chloride, stir the reaction at 10-15 ℃ for 5h. Recover methanol to dryness, add dilute hydrochloric acid to boil, and filter to obtain p-nitrobenzamidine hydrochloride solution. 2. Reduction Heat the above solution to 50 ℃, add Glacial acetic acid, iron powder was slowly added at 60°C. After completion, the temperature was raised to 105°C for 5h. Filtration, the filtrate was basified with sodium hydroxide solution to pH 12. Filtered, and the filtrate was acidified again with hydrochloric acid to pH 1- 2. Concentrate, cool and crystallize, and filter to obtain p-aminobenzamidine hydrochloride. 3. For diazotization and coupling, first add half the amount of p-aminobenzamidine hydrochloride to water, add hydrochloric acid to dissolve, at -5～0℃ Add 10% sodium nitrite solution dropwise, check the end point with potassium iodide starch test paper, mix the other half of p-aminobenzimididine hydrochloride with a small amount of water and add it, then add saturated sodium acetate to precipitate a yellow precipitate. Filter and filter The cake is dissolved in water, and the pH is adjusted to 9-10 with 10% sodium hydroxide solution to precipitate crystals. Filter and wash the filter cake with cold water and methanol to obtain 1, 3-bis(p-amidinobenzene)-triazene. 4 Salt formation After stirring the above-mentioned triazene, acetylglycine and methanol for 0.5h, adjust the pH to 7 with ammonia water and raise the temperature to dissolve. Add activated carbon, filter, and the filtrate is cooled and crystallized. Filter and dry to obtain diamidine.

Uses

An anti-protozoal and anti-trypanosomal compound

Use Classification：

Veterinary Drug -> TRYPANOCIDE; -> JECFA Functional Classes

Food Additive Classes：

Veterinary Drug -> TRYPANOCIDE;

Computed Properties

Molecular Weight:398.4
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:7
Exact Mass:398.18148659
Monoisotopic Mass:398.18148659
Topological Polar Surface Area:203
Heavy Atom Count:29
Complexity:500
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Material

4-Nitrobenzoic acid

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