MA41732B1 - Thiazolylbenzimidazole-derived molecules containing triazoles and their uses for the treatment of cancer - Google Patents

Thiazolylbenzimidazole-derived molecules containing triazoles and their uses for the treatment of cancer

Info

Publication number
MA41732B1
MA41732B1 MA41732A MA41732A MA41732B1 MA 41732 B1 MA41732 B1 MA 41732B1 MA 41732 A MA41732 A MA 41732A MA 41732 A MA41732 A MA 41732A MA 41732 B1 MA41732 B1 MA 41732B1
Authority
MA
Morocco
Prior art keywords
thiazolylbenzimidazole
synthesis
cancer
treatment
1hbenzo
Prior art date
Application number
MA41732A
Other languages
French (fr)
Other versions
MA41732A1 (en
Inventor
Rachid Bouhfid
Abou El Kacem Qaiss
Nawal Merghoub
Bourkadi Khadija El
Original Assignee
Moroccan Foundation For Advanced Science Innovation And Res Mascir
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Moroccan Foundation For Advanced Science Innovation And Res Mascir filed Critical Moroccan Foundation For Advanced Science Innovation And Res Mascir
Priority to MA41732A priority Critical patent/MA41732B1/en
Priority to PCT/MA2018/050019 priority patent/WO2019132638A1/en
Publication of MA41732A1 publication Critical patent/MA41732A1/en
Publication of MA41732B1 publication Critical patent/MA41732B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne la synthèse d’unenouvelle classe des molécules poly hétérocycliques dérivés du thiazolylbenzimidazole contenant le motif triazolique via plusieurs étapes de synthèse, ainsi que l’utilisation de ces molécules dans le domaine de la santé pour le traitement du cancer. Premièrement, la synthèse de la 4-(1-(prop-2-yn-1-yl)-1hbenzo[d]imidazole-2-yl)thiazole(1) par uneréaction d’alkylation de thiazolylbenzimidazole dans les conditions de la catalyse par transfert de phase avec le bromure de propargyle, deuxièmement, préparation des azides avec l’azoture de sodium et le bromure d’alkyle et troisièmement, la synthèse de4-(1-((1-alkyl-1h-1,2,3-triazol-4-yl)méthyl)-1hbenzo[d]imidazol-2-yl)thiazole par une réaction de cycloaddition 1,3-dipolaire dans les conditions de la chimie clic. Quatrièmement, la quaternisation des cycloadduits avec iodométhane à reflux, à fin d’augmenter la solubilité de ces produits.The present invention relates to the synthesis of a new class of polyheterocyclic molecules derived from thiazolylbenzimidazole containing the triazole unit via several synthetic steps, as well as the use of these molecules in the field of health for the treatment of cancer. First, the synthesis of 4- (1- (prop-2-yn-1-yl) -1hbenzo [d] imidazol-2-yl) thiazole (1) by an alkylation reaction of thiazolylbenzimidazole under the conditions of catalysis by phase transfer with propargyl bromide, second, preparation of azides with sodium azide and alkyl bromide and third, synthesis of 4- (1 - ((1-alkyl-1h-1,2,3 -triazol-4-yl) methyl) -1hbenzo [d] imidazol-2-yl) thiazole by a 1,3-dipolar cycloaddition reaction under the conditions of click chemistry. Fourth, the quaternization of the cycloadducts with iodomethane at reflux, in order to increase the solubility of these products.

MA41732A 2017-12-28 2017-12-28 Thiazolylbenzimidazole-derived molecules containing triazoles and their uses for the treatment of cancer MA41732B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
MA41732A MA41732B1 (en) 2017-12-28 2017-12-28 Thiazolylbenzimidazole-derived molecules containing triazoles and their uses for the treatment of cancer
PCT/MA2018/050019 WO2019132638A1 (en) 2017-12-28 2018-12-28 Molecules derived from thiazolylbenzimidazole containing triazoles and their uses for the treatment of cancer.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MA41732A MA41732B1 (en) 2017-12-28 2017-12-28 Thiazolylbenzimidazole-derived molecules containing triazoles and their uses for the treatment of cancer

Publications (2)

Publication Number Publication Date
MA41732A1 MA41732A1 (en) 2019-08-30
MA41732B1 true MA41732B1 (en) 2020-06-30

Family

ID=65352065

Family Applications (1)

Application Number Title Priority Date Filing Date
MA41732A MA41732B1 (en) 2017-12-28 2017-12-28 Thiazolylbenzimidazole-derived molecules containing triazoles and their uses for the treatment of cancer

Country Status (2)

Country Link
MA (1) MA41732B1 (en)
WO (1) WO2019132638A1 (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010108187A2 (en) * 2009-03-20 2010-09-23 Brandeis University Compounds and methods for treating mammalian gastrointestinal microbial infections
EP2698367A1 (en) * 2012-08-14 2014-02-19 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Benzimidazoles for the treatment of cancer

Also Published As

Publication number Publication date
WO2019132638A1 (en) 2019-07-04
MA41732A1 (en) 2019-08-30

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