17395-31-2

Basic information

• Product Name: 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide
• Synonyms: 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide
• CAS NO: 17395-31-2
• Molecular Formula: C16H18Br2ClN3O3
• Molecular Weight: 495.59342
• EINECS: 241-422-7
• Mol File: 17395-31-2.mol

Chemical Properties

• Boiling Point: 595.8°Cat760mmHg
• Flash Point: 314.1°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 4.84E-15mmHg at 25°C
• CAS DataBase Reference: 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide(17395-31-2)
• EPA Substance Registry System: 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide(17395-31-2)

Safety Data

• Hazardous Substances Data: 17395-31-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide is used as a potential pharmaceutical agent for its diverse structural features that may allow it to interact with various biological targets such as enzymes or receptors. Its ability to form hydrogen bonds and interact with charged molecules could be beneficial in the development of new drugs targeting specific diseases or conditions.
Used in Drug Design and Development:
In the field of drug design and development, 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide can be utilized as a starting point for the synthesis of new compounds with improved pharmacological properties. Its unique structural elements may provide insights into the design of more effective and selective drugs, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Research:
7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide serves as a valuable subject for chemical research, particularly in the study of quinazolinone-based compounds and their interactions with biological systems. Understanding the properties and potential applications of 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide can contribute to the advancement of knowledge in the field of chemistry and its applications in various industries.

InChI:InChI=1/C16H17BrClN3O3.BrH/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14;/h5-6,8,14-15,19,23H,1-4,7H2;1H

Upstream product

• 108-41-8 1-chloro-3-methylbenzene 
• 150812-32-1 2-amino-4-bromo-5-chlorobenzoic acid 
• 17518-98-8 7-bromo-6-chloro-3,4-dihydroquinazolin-4-one 
• 64544-01-0 7-bromo-6-chloro-3-[3-(3-hydroxyl-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one 
• 68471-58-9 1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine 
• 64544-00-9 2,3-cis-2-bromoacetonyl-3-methoxy-1-piperidinecarboxylic acid allyl ester 

Downstream Products

• 55837-20-2 halofuginone 
• 55837-20-2 (+)-halofuginone 

Relevant articles and documents

New synthesis process for preparing veterinary bulk drug halofuginone hydrobromide

The invention discloses a process method for preparing veterinary raw material drug halofuginone hydrobromide, and relates to the field of veterinary drugs and the technical field of drug synthesis. According to the invention, a novel process route is adopted, 7-bromo-3-(8-bromo-5-hydroxy-2-oxo-3-octenyl)-6-chloro-4 (3H)-quinazolinone is taken as a starting raw material, and the halofuginone hydrobromide is prepared through three-step reaction of ammonolysis, purification and salification, so that the problems of difficulty in obtaining raw materials, harsh reaction conditions, high cost and the like in the existing synthesis method are solved. The novel synthesis process for preparing the veterinary drug halofuginone hydrobromide is simple in process operation, low in production cost, few in steps, high in total yield, small in pollution and suitable for industrial mass production.

Stereoselective total synthesis of all the stereoisomers of (+)- and (?)-febrifugine and halofuginone

A convenient method for the total synthesis of all the stereoisomers of febrifugine and halofuginone using D-arabinose and L-arabinose as the key starting materials is reported. Apart from the inherent stereocenters in these pentose sugars, the method utilizes the selective hydrogenolysis of the anomeric O-benzyl group, stereoselective Grignard reaction and Wacker oxidation as the key steps to obtain the important precursors for the total synthesis.

Preparation method of trans-halofuginone hydrobromide and intermediate thereof

The invention relates to a preparation method of trans-halofuginone hydrobromide and an intermediate thereof, wherein the method comprises the following steps: (1) carrying out a reaction of a compound represented by the formula (V) with a compound represented by the formula (IV) in a methanol solution under the action of sodium carbonate to obtain an intermediate (III); (2) adding the intermediate (III) into an HBr aqueous solution, heating to 100-115 DEG C, carrying out a reaction for 2-3 h, cooling the reaction solution to 70-80 DEG C, adding the HBr aqueous solution, heating to 100-115 DEGC, and carrying out a reaction for 1-3 h to obtain an intermediate (II); and (3) dispersing the intermediate (II) in an alcoholic solution, heating to 70-85 DEG C, and carrying out a stirring reaction to obtain the compound represented by the formula (I).

Synthetic method for halofuginone and intermediate of halofuginone

The invention relates to a synthetic method for halofuginone and an intermediate of the halofuginone. The reaction formula is shown in the description, wherein R1 is one selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and t-butyl; R2 is one selected from the group consisting of methyl and ethyl; and R3 is one selected from the group consisting of methoxyformyl, ethoxyformyl, tert-butoxyformyl, benzyloxyformyl, trichloroethoxyformyl and benzyl. The synthetic method provided by the invention has the advantages of a simple process, low costs, few by-products in the synthetic process, a simple purification process, no need of column chromatography purification, a high product yield, less impurities, high purity, and controllable product quality, easily meets ICH declaration requirements and can be used for industrial production of the halofuginone.

A convergent strategy towards febrifugine and related compounds

We report a modular five step synthetic route to the febrifugines that employs 2-(chloromethyl)allyl-trimethylsilane as a conjunctive reagent for the coupling of the piperidine and quinazolinone groups. We also demonstrate the application of a recent Rh-catalyzed quinazolinone synthesis for the facile generation of febrifugine analogs.

A novel synthesis of the efficient anti-coccidial drug halofuginone hydrobromide

Background: Halofuginone hydrobromide (1) is recognized as an effective drug against several species of Eimeria (E.) in poultry. In this paper, we describe a convenient and low cost preparation method for the compound, as well as primary validation of its activity. Methods: First, 7-bromo-6-chloroquinazolin-4(3H)-one (2) was prepared from m-chlorotoluene by a conventional process, and then chloroacetone was creatively introduced in two steps. Finally, halofuginone hydrobromide (1) was obtained from 7-bromo-6-chloro-3-(3-cholroacetonyl) quinazolin-4(3H)-one (4) by a four-step reaction sequence including condensation, cyclization, deprotection and isomerization. The structures of the relative intermediates and target compound were characterized by melting point, IR, MS and 1H-NMR. Besides, the protective effect of compound 1-supplemented chicken diet at doses of 6, 3 and 1.5 mg per 1 kg were evaluated on chickens infected with E. tenella, by reduction in mortality, weight loss, fecal oocyst excretion and gut pathology, respectively. Results: Halofuginone hydrobromide (1) was prepared successfully by and improved and innovative method based on traditional research. Moreover, the synthesized halofuginone hydrobromide significantly exhibited an anti-coccidial property. Conclusions: The fruitful work described in this Communication has resulted in halofuginone hydrobromide, which has a good pharmaceutical development prospects, becoming more available for large-scale production.

An asymmetric synthesis of febrifugine, halofuginone and their hemiketal isomers

A new synthesis of both enantiomers of naturally occurring febrifugine (1) and its analogue halofuginone (3) are reported. This robust route relies on an enzymatic kinetic resolution (EKR)-cross metathesis (CM) sequence, performed on allylic alcohol 8. A diastereoselective Lewis acid-mediated cyclisation of resultant enone 6 affords piperidine 12. In relation to its enantiomeric excess, values of 87 and 88% e.e were obtained for both enantiomers of 12 and for (?)-12 this was increased to 98% e.e by conducting the resolution process twice. A bromination (featuring an in situ temporary alcohol protection), alkylation and amino-deprotection sequence finally afforded the target compounds (+)- and (?)-1, and (+)- and (?)-3. Studies demonstrate that, as their ammonium salts, the compounds are stereochemically stable. However, as their free-bases, particularly in chloroform, C-2 isomerisation occurs. This isomerisation has been taken advantage of synthetically to provide enantioenriched (+)-isofebrifugine (2) and both enantiomers of isohalofuginone (14).

PHARMACEUTICAL COMPOSITIONS OF THE ISOLATED D- ENANTIOMER OF THE QUINAZOLINONE DERIVATIVE HALOFUGINONE

The present invention relates to pharmaceutical compositions comprising as an active ingredient an isolated, chirally pure D-enantiomer of the quinazolinone derivative halofuginone having increased therapeutic activity and decreased side effects compared to the corresponding racemic mixtures, the composition being substantially free of the L-enantiomer and useful in the treatment of diseases and disorders associated with fibrotic conditions or cell proliferation.

Novel quinazolinone

The novel product, dextrorotary 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-acetonyl]-4(3H)-quinazolinone and its non-toxic, pharmaceutically acceptable acid addition salts having anticoccidiosis activity and its preparation and use.