10314-06-4Relevant articles and documents
Synthesis of pyrazoles based on functionalized allenoates
Sakhautdinov, Ilshat M.,Gumerov, Aynur M.,Batyrshin, Ilnur R.,Fatykhov, Akhnaf A.,Suponitsky, Kyrill Yu.,Yunusov, Marat S.
, p. 641 - 651 (2014)
Regiospecific synthesis of pyrazole-3-carboxylate derivatives by 1,3-dipolar cycloaddition of diazomethane with allenoates in presence of triethylamine is demonstrated. Reaction of allenoates with stearic acid moiety containing diazoketone is explored under ultrasonic conditions. Novel derivatives of pyrazole were achieved in excellent yields.
Synthesis and anticonvulsant activity of N,N-phthaloyl derivatives of central nervous system inhibitory amino acids
Usifoh, Cyril O.,Lambert, Didier M.,Wouters, Johan,Scriba, Gerhard K.E.
, p. 323 - 331 (2001)
In order to study the influence of the length of the amino acid chain of N,N-phthaloyl-amino acid amides as analogues of the former anticonvulsant taltrimide on the seizure-antagonizing activity glycine, β-alanine and γ-aminobutyric acid (GABA) derivatives were synthesized. The corresponding taurine derivatives were also included. Generally, the glycine-derived amides showed a higher activity than the β-alanine and GABA derivatives in the maximal electroshock seizure (MES) test in mice upon intraperitoneal administration. The activity was comparable to the respective taurine derivatives. The N,N-phthaloyl-glycine amides were also active in the MES test upon oral administration to rats. No significant activity was noted in the seizure threshold test with subcutaneous pentylene-tetrazole. The ED50 of N,N-phthaloyl-glycine ethyl amide (4b) in the MES test upon intraperitoneal administration to mice was 19.1 mg/kg. On a molar basis this activity is comparable to the activity of phenytoin with little toxicity in the rotorod test. In conclusion, N,N-phthaloyl-glycine amides might represent promising antiepileptic drugs.
Aminoalkyl-1,1-bis(phosphinic acids): Stability, acid-base, and coordination properties
David, Tomá?,Procházková, Soňa,Kotek, Jan,Kubí?ek, Vojtěch,Hermann, Petr,Luke?, Ivan
, p. 4357 - 4368 (2014)
Four geminal bis(phosphinic acids), namely, aminomethylbis(H-phosphinic acid) (H2L1) and 4-aminobutyl-1-hydroxy-1,1-bis(R-phosphinic acid) with R = H (H2L2), Me (H2L3) and CH2CH2COOH (H4L4), were studied. Their acid-base properties and coordination ability towards Cu2+, Ni2+ and Zn2+ ions were studied by potentiometry, UV/Vis spectroscopy and NMR spectroscopy. The amine group in H2L1 has a lower protonation constant (log Ka = 6.79) than those found for other studied bisphosphinates (log Ka = 10.75-11.05) with distant amine groups. The structure of [Ca(H2L2-O,O')(HL2-O,O')]Cl revealed an octahedral arrangement of the metal coordination sphere and a linear polymeric structure, which forms through eight-membered Ca(-O-P-O-)2Ca rings. The structure of [Cu(HL3-O,O')2(H2O)]·5H2O shows two chelating bisphosphinate groups in an equatorial O4 environment. The structure of [Cu(H0.5L3-O,O')(NO3)0.5]·2.25H2O shows two different coordination environments, one is an elongated tetragonal pyramid, and the other is a trigonal bipyramid with a bidentate nitrate ion. Four geminal bisphosphinates were synthesized, and their acid-base properties and coordination behaviour with Cu2+, Zn2+ and Ni2+ ions were studied. The compounds show lower amine basicity and complex stability constants than those of analogous bisphosphonates. In the solid-state structures of the Ca2+ and Cu2+ complexes, the bisphosphinates are coordinated in O,O'-chelating mode.
AMD070, a CXCR4 chemokine receptor antagonist: Practical large-scale laboratory synthesis
Crawford, Jason B.,Chen, Gang,Gauthier, David,Wilson, Trevor,Carpenter, Bryon,Baird, Ian R.,McEachern, Ernie,Kaller, Alan,Harwig, Curtis,Atsma, Bem,Skerlj, Renato T.,Bridger, Gary J.
, p. 823 - 830 (2008)
An efficient and convergent four-step synthetic route to the CXCR4 chemokine receptor antagonist AMD070 (1) has been developed which employs only a single chromatographic step in the entire sequence. Novel reductive amination methods have been developed for the coupling of 2 and 3 in which a dehydrative imine formation is followed by reduction with an attenuated borohydride reagent (zinc chloride and sodium borohydride). Selective extraction methods were employed to purify synthetic intermediates and remove reagents and impurities. A procedure has also been developed to isolate 1 in a pure crystalline form.
Highly Stereoselective Synthesis of Isoindole Derivatives Containing an Azetidinone Ring
Hosseinkhani, Batool,Islami, Mohammad Reza,Hosseinkhani, Saman
, p. 2277 - 2279 (2015)
Isoindole derivatives containing an azetidin-2-one moiety were prepared from phthalic anhydride by an approach that involves a [2π+2π] cycloaddition of an imine to a novel ketene generated in situ, and an electrocyclic reaction of a zwitterionic intermediate. The reactions were highly stereoselective and trans-β-lactams were obtained as the sole observed products.
α-Amino acid derived bisphosphonates. Synthesis and anti-resorptive activity
Mizrahi, Dana M.,Waner, Trevor,Segall, Yoffi
, p. 1 - 25 (2001)
Eleven new bisphosphonates were prepared from naturally-occurring l-amino acids. The synthesis required special attention to amino and side-chain protections. The novel compounds were tested in TPTX (thyroparathyroidectomized) rats against arotinoid-induced hypercalcemia and were compared to alendronate. Most of the compounds showed moderate to no anti-resorptive activity. Two compounds were more active than clodronate, but less than alendronate. Limited SAR conclusions were drawn.
A practical synthesis of alendronate sodium through counterattack reaction
Seki, Masahiko
, p. 1556 - 1558 (2012)
An efficient synthesis of alendronate sodium, an osteoporosis drug, has been developed through counterattack reaction' involving treatment of the respective acyl phosphonate with (MeO) and TMSBr followed by deblocking with aqueous HCl.
MACROCYCLIC COMPOUNDS AS STING AGONISTS AND METHODS AND USES THEREOF
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Paragraph 0261-0262, (2021/01/29)
Disclosed are macrocyclic compounds having the general Formula (I) or (II) and their tautomeric forms, stereoisomers, pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof, and their combination with suitable medicament, corresponding processes for the synthesis and pharmaceutical compositions and uses of compounds disclosed herein.
Rh(III)-Catalyzed C-H Amidation of Arenes with N-Methoxyamide as an Amidating Reagent
Ju, Guodong,Li, Guobao,Qian, Guanwen,Zhang, Jingyu,Zhao, Yingsheng
supporting information, p. 7333 - 7336 (2019/10/08)
The Rh(III)-catalyzed amidation of C(sp2)-H bonds has been reported by employing the N-methoxyamide as a novel amino source. An excellent level of functional group tolerance can be achieved when N-methoxyamide derivatives are used as the amidating reagents. Importantly, several known bioactive compounds such as Aminalon, Pregabalin, Gabapentin, and Probenecid can be transformed to effective amidating reagents, as a way to facilitate the development of new bioactive molecules.
