Synthesis of a New Type of1,1-Bisphosphonates Bearing S-, and N-Heterocycles, Based on theReactions of Methylenebisphosphonate with Alkenes

Abdou, Wafaa M.; Ganoub, Neven A.; El-Khoshnieh, Yehia O.

doi:10.1055/s-2003-38729

Cited by 12 publications

(5 citation statements)

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“…Our contribution to this field of BPs that started in 2002 included synthesis of a series of BPs for the treatment of bone resorption disorder 7–14. Indeed, all BPs have significant potency on bone resorption.…”

Section: Introductionmentioning

confidence: 99%

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Abdou

Khidre

Kamel

2011

Archiv der Pharmazie

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Methylenebisphosponic acid tetraethyl ester (1) was added to 2-azido-7a-e and 2-chloroquinoline-3-chalcones 10a-e in boiling sodium ethanolate solution to give, via Michael addition, tetrazolo[1,5-a]quinoline-8a-d, 13a and 2-chloroquinoline-based bisphosphonates 11a-d, 14a in E-configuration. Further acid hydrolysis afforded the respective BP-acid analogues E-9a-d, 12a-d, 13b, and 14b in excellent yields. Anti-tumor activity screening for the new BP-acids at a dose of 10 µM utilizing 44 different human tumor cell lines representing breast, ovary, prostate, lung, and CNS cancer as well as leukemia and melanoma was carried out. Eight of ten tested compounds exhibited remarkable anti-tumor activity against breast and prostate cancer, and a promising anti-tumor sensitivity toward ovarian cancer and melanoma. Conversely, there was only scattered activity against leukemia and no noticeable action of these BP-acids on CNS or lung cancer. Based on the prediction results (PASS program), anti-inflammatory activity of the new acids was also determined in vivo, by the acute carrageenin induced paw edema in rats. Many of these compounds showed anti-inflammatory properties at a dose of 50 mg/kg body weight.

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Section: Introductionmentioning

confidence: 99%

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Abdou

Khidre

Kamel

2011

Archiv der Pharmazie

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“…Previous work has reported the synthesis of substituted 1,1-bisphosphonic acid through hydrolysis of the cor- Scheme 2. responding bisphosphonate product with concentrated hydrochloric acid [18]. The present study showed that substituted 1,1-bisphosphonic acids can be synthesized directly from the reaction of 4-arylidene-2-phenyl-5(4H)-oxazolone derivatives 1a, b with bisphosphonate 2 using concentrated hydrochloric acid (cf.…”

Section: Introductionmentioning

confidence: 80%

Synthesis of New Bisphosphonate and Bisphosphonic Acid Derivatives and Heterocyclic and Dialkylcarbamoyl Oxazolone Derivatives with Anticancer and Antischistosomal Activity

Boulos

Ewies

Fahmy

2011

Zeitschrift Für Naturforschung B

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The reaction of 5(4H)-oxazolones with tetraethyl methanediylbis(phosphonate) afforded new 1,1-bisphosphonate and 1,1-bisphosphonic acid derivatives. Moreover, 5(4H)-oxazolones reacted with Wittig reagents to give the corresponding heterocyclic products. Treatment of 5(4H)-oxazolones with trisdialkylaminophosphanes gave the corresponding N-(1-dialkylcarbamoyl)-2-phenylvinylbenzamides. Mechanisms accounting for the formation of the new products are discussed. The biological activity of the newly synthesized compounds was also examined.

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“…The DBU-assisted oxathiaphospholane ring opening process did not cause any measurable C-racemization of phosphorothioylated/phosphorylated amino acids (Scheme 23). The addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, provided allylic monophosphates (108), (109) and (110) with enantiomeric excess of up to 87, 94 and 498%, respectively (Scheme 28). 49 Non-enzymatic systems were used to show that vibrational spectroscopy can provide a sensitive probe of the environment of the phosphoryl group, a group commonly transferred in enzymatic catalysis.…”

Section: Scheme 13mentioning

confidence: 99%

“…106 The first synthesis of phosphonoacrolein (209) was achieved by acid decomposition of b-ethoxy-a-(methoxymethyl)vinylphosphonate (210) derived from lithiated phosphonate (211) and chloromethyl methyl ether (MOMCL) (Scheme 58). 110 Alkenylphosphonates (226) can be prepared by regioselective addition of monoesters of phosphonic acid (227) to alkynes in the presence of Hg(OAc) 2 / BF 3 OEt 2 (Scheme 61). New families of dihydropyrans (212), (213), (214) and pyranopyrans (215) have been obtained in this way (Figure 38).…”

Section: Scheme 41mentioning

confidence: 99%

Organophosphorus Chemistry

Hall

Bricklebank

Grampel³

et al. 2006

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Organophosphorus compounds are ubiquitous in nature, and due to their innate chemical properties, serve a fundamental role in a number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new heights. This Thematic Series highlights and details some of the novel methods that are advancing the field of organophosphorus chemistry.The Thematic Series covers topics that range from new synthetic methods and phosphorus-based ligands in asymmetric catalysis to bisphosphonates as promising enzyme inhibitors. More specifically, the Thematic Series spans new methods in C-P bond formation, chiral phosphines in nucleophilic organocatalysis, chiral N-phosphinyl auxiliaries, cyclic phosphonamide reagents in the total synthesis of natural products, phosphinate-containing heterocycles, new routes to phosphinoyl-indoles and phosphinoyl-isocoumarins and new chemistries of H-phosphonates. The Thematic Series also details work on new metathesis-based reactions of vinyl phosphonates and phosphate tethers, novel phosphorus-based ligands in asymmetric catalysis, novel rasta resin-triphenylphosphine oxides and their use as recyclable heterogeneous reagents, the Atherton-Todd reaction, cyclic phosphonium ionic liquids with distinct properties, photo-removable phosphate protecting groups, new methods of C-H functionalization using phosphoryl-related directing groups, the exciting chemistry of substituted phosphanylidenecarbenes and phosphoryl azides, and bisphosphonate ethers as promising inhibitors of geranylgeranyl diphosphate synthase (GGDPS).The articles and reviews capture the emerging potential of organophosphorus compounds and exciting opportunities in the field, and hopefully, will inspire and motivate investigators in the field to investigate new chemistry in this area. Taken collectively, organophosphorus chemistry embodies a broad, vibrant and continual growing scientific area with this Thematic Series highlighting recent advances in the field. We are grateful and indebted to the authors for their hard work and exciting contri-

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Synthesis of a New Type of1,1-Bisphosphonates Bearing S-, and N-Heterocycles, Based on theReactions of Methylenebisphosphonate with Alkenes

Cited by 12 publications

References 2 publications

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Synthesis of New Bisphosphonate and Bisphosphonic Acid Derivatives and Heterocyclic and Dialkylcarbamoyl Oxazolone Derivatives with Anticancer and Antischistosomal Activity

Organophosphorus Chemistry

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