876-53-9Relevant academic research and scientific papers
An improved synthesis of diiodonoradamantane
Ioannou, Savvas,Nicolaides, Athanassios V.
, p. 6938 - 6940 (2009)
Τhe synthesis of 3,7-diiodo-tricyclo[3.3.1.03,7]nonane, the main precursor of noradamantene, by iodination of the corresponding diol via its dimesylate affords a threefold higher yield than the direct iodination of the diol. Neither the dimesylate nor the cyclic sulfate of the diol yields noradamantene upon reduction with sodium amalgam.
Polymerization kinetics of adamantane-based dicyanate ester and thermal properties of resulting polymer
Galukhin, Andrey,Islamov, Daut,Nikolaev, Ilya,Nosov, Roman,Taimova, Guzel,Vyazovkin, Sergey
, (2021/06/15)
The kinetics of liquid-state polymerization of adamantane-based dicyanate ester has been studied for the first time by means of conventional and temperature-modulated DSC. It has been detected that the later stages of polymerization undergo a transition from kinetic- to diffusion-controlled regime. Detailed analysis of the polymerization kinetics in the reaction-controlled regime has revealed that the process rate can be well described in the frameworks of the presently proposed autocatalytic quasi-one-step model. The proposed model eliminates arbitrarily guessing the value for the initial conversion that provides a reasonable alternative to the broadly used truncated Sestak-Berggren model. The adamantane-based dicyanate ester polymerization product demonstrates markedly higher thermal stability and glass transition temperature compared to those of dicyanate esters with flexible hydrocarbon bridging units. The obtained experimental results confirm our hypothesis about the influence of the rigidity of cyanate ester molecule on its reactivity and thermal properties of the corresponding polymer product.
Synthetic method of saxagliptin intermediate (by machine translation)
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Paragraph 0033-0036, (2020/11/23)
(1) The compound 1 is reacted under the action of sodium ethoxide in a substitution reaction under the action of sodium ethoxide to form compound 2 by stirring and refluxing 2 under the action of sodium ethoxide to form compound 2; (8 hours) compound 3 is reacted 3 at room temperature under the alkaline condition by adding L - arginine to obtain a salvildagliptin intermediate, compound 3) and liquid bromine under the action of sodium ethoxide and then adding L-arginine under the action of sodium ethoxide under the action of sodium ethoxide and then 8 hours adding L-arginine 4 under the 4 action of 4 sodium ethoxide 12 hours. Raw materials and reagents are cheap and easily available, the reaction operation is simple, the reaction conditions are mild, the yield is high, the quality is good, the resolution end product can reach 99% ee values, and the requirements of drug intermediates are met. (by machine translation)
Decarboxylative Bromination of Sterically Hindered Carboxylic Acids with Hypervalent Iodine(III) Reagents
Kanazawa, Junichiro,Koyamada, Kenta,Miyamoto, Kazunori,Uchiyama, Masanobu,Watanabe, Ayumi
supporting information, p. 1328 - 1334 (2020/08/14)
Sterically hindered three-dimensional (3D) alkyl halides are promising precursors for various reactions; however, they are difficult to synthesize via conventional reactions. We present an efficient and practical method for decarboxylative bromination of sterically hindered 3D aliphatic carboxylic acids using commercially available (diacetoxyiodo)benzene and potassium bromide, one of the most stable and cheapest bromine sources in nature. The present method features a metal-free/Br2-free system, mild reaction conditions, one-pot operation under air at room temperature, wide functional group compatibility, and gram-scale synthetic capability. This highly efficient reaction cleanly converts a broad range of carboxylic acids, the most inexpensive and readily available sources of highly strained/naturally occurring/drug-related scaffolds, into the corresponding alkyl bromides in good to high yields.
Synthesis and cytotoxicity of novel simplified eleutherobin analogues as potential antitumour agents
Sosonyuk, Sergey E.,Peshich, Anita,Tutushkina, Anastasia V.,Khlevin, Dmitry A.,Lozinskaya, Natalia A.,Gracheva, Yulia A.,Glazunova, Valeria A.,Osolodkin, Dmitry I.,Semenova, Marina N.,Semenov, Victor V.,Palyulin, Vladimir A.,Proskurnina, Marina V.,Shtil, Alexander A.,Zefirov, Nikolay S.
supporting information, p. 2792 - 2797 (2019/03/12)
Mixed simplified structures containing the paclitaxel and eleutherobin pharmacophore moieties were analyzed using molecular docking techniques and synthesized based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds. The crucial role of substituents' stereochemistry in biological activity is discussed. At micromolar concentrations the selected analogues interfered with tubulin dynamics in vitro and in a living organism. Furthermore, new compounds were cytotoxic against human tumour cell lines. The simplified eleutherobin analogues may be considered as prototypes of a new class of antitumour agents.
Temperature Controls Guest Uptake and Release from Zn4L4 Tetrahedra
Zhang, Dawei,Ronson, Tanya K.,Güryel, Songül,Thoburn, John D.,Wales, David J.,Nitschke, Jonathan R.
supporting information, p. 14534 - 14538 (2019/10/11)
We report the preparation of triazatruxene-faced tetrahedral cage 1, which exhibits two diastereomeric configurations (T1 and T2) that differ in the handedness of the ligand faces relative to that of the octahedrally coordinated metal centers. At lower temperatures, T1 is favored, whereas T2 predominates at higher temperatures. Host-guest studies show that T1 binds small aliphatic guests, whereas T2 binds larger aromatic molecules, with these changes in binding preference resulting from differences in cavity size and degree of enclosure. Thus, by a change in temperature the cage system can be triggered to eject one bound guest and take up another.
KOtBu as a single electron donor? Revisiting the halogenation of alkanes with CBr4 and CCl4
Emery, Katie J.,Young, Allan,Arokianathar, J. Norman,Tuttle, Tell,Murphy, John A.
supporting information, (2018/05/22)
The search for reactions where KOtBu and other tert-alkoxides might behave as single electron donors led us to explore their reactions with tetrahalomethanes, CX4, in the presence of adamantane. We recently reported the halogenation of adamantane under these conditions. These reactions appeared to mirror the analogous known reaction of NaOH with CBr4 under phase-transfer conditions, where initiation features single electron transfer from a hydroxide ion to CBr4. We now report evidence from experimental and computational studies that KOtBu and other alkoxide reagents do not go through an analogous electron transfer. Rather, the alkoxides form hypohalites upon reacting with CBr4 or CCl4, and homolytic decomposition of appropriate hypohalites initiates the halogenation of adamantane.
Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases
Liu, Zheng,Yang, Si,Jin, Xiaoyong,Zhang, Gaoxiao,Guo, Baojian,Chen, Haiyun,Yu, Pei,Sun, Yewei,Zhang, Zaijun,Wang, Yuqiang
supporting information, p. 135 - 147 (2017/02/05)
A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized. These compounds combined the memantine skeleton and a nitrate moiety, and thus inhibited the N-methyl-d-aspartic acid receptor and released NO in the central nervous system. The biological evaluation results revealed that the new memantine nitrates were effective in protecting neurons against glutamate-induced injury in vitro. Moreover, memantine nitrates dilated aortic rings against phenylephrine-induced contraction. The structure-activity relationships of neuroprotection and vasodilation were both analyzed. In further studies, compound MN-05 significantly protected cortical neurons by inhibiting Ca2+ influx, reducing free radical production and maintaining the mitochondrial membrane potential. Further research on MN-05 is warranted.
Bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds
Khusnutdinov,Shchadneva,Khisamova
, p. 184 - 187 (2015/04/14)
Catalytic bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds has been performed. The favorable ratio of catalyst and reagents and the conditions of a selective synthesis of bromine-substituted adamantanes have been developed.
Mixed-ligand hydroxocopper(II)/pyridazine clusters embedded into 3D framework lattices
Degtyarenko, Anna S.,Handke, Marcel,Kraemer, Karl W.,Liu, Shi-Xia,Decurtins, Silvio,Rusanov, Eduard B.,Thompson, Laurence K.,Krautscheid, Harald,Domasevitch, Konstantin V.
supporting information, p. 8530 - 8542 (2014/06/09)
Rational combination of pyridazine, hydroxo and carboxylate bridging ligands led to the assembly of three types of mixed-ligand polynuclear Cu(ii) clusters (A: [Cu2(μ-OH)(μ-pdz)(μ-COO)]; B: [Cu 4(μ3-OH)2(μ-pdz)2]; C: [Cu5(μ-OH)2(μ-pdz)4(μ-COO) 2(μ-H2O)2]) and their integration into 3D framework structures. Mixed-ligand complexes [Cu2(μ-OH){TMA}(L) (H2O)] (1), [Cu4(μ3-OH)2{ATC} 2(L)2(H2O)2]·H2O (2) [Cu4(μ3-OH)2{TDC}3(L) 2(H2O)2]·7H2O (3) (L = 1,3-bis(pyridazin-4-yl)adamantane; TMA3- = benzene-1,3,5- tricarboxylate, ATC3- = adamantane-1,3,5-tricarboxylate, TDC 2- = 2,5-thiophenedicarboxylate) and [Cu5(μ-OH) 2{X}4(L)2(H2O)2] ·nH2O (X = benzene-1,3-dicarboxylate, BDC2-, n = 5 (4) and 5-hydroxybenzene-1,3-dicarboxylate, HO-BDC2-, n = 6 (5)) are prepared under hydrothermal conditions. Trigonal bridges TMA3- and ATC3- generate planar Cu(ii)/carboxylate subtopologies further pillared into 3D frameworks (1: binodal 3,5-coordinated, doubly interpenetrated tcj-3,5-Ccc2; 2: binodal 3,8-coordinated tfz-d) by bitopic pyridazine ligands. Unprecedented triple bridges in 1 (cluster of type A) support short Cu...Cu separations of 3.0746(6) A. The framework in 3 is a primitive cubic net (pcu) with multiple bis-pyridazine and TDC2- links between the tetranuclear nodes of type B. Compounds 4 and 5 adopt uninodal ten-coordinated framework topologies (bct) embedding unprecedented centrosymmetric open-chain pentanuclear clusters of type C with two kinds of multiple bridges, Cu(μ-OH)(μ-pdz)2Cu and Cu(μ-COO)(μ-H2O)Cu (Cu...Cu distances are 3.175 and 3.324 A, respectively). Magnetic coupling phenomena were detected for every type of cluster by susceptibility measurements of 1, 3 and 4. For binuclear clusters A in 1, the intracluster antiferromagnetic exchange interactions lead to a diamagnetic ground state (J = -17.5 cm-1; g = 2.1). Strong antiferromagnetic coupling is relevant also for type B, which consequently results in a diamagnetic ground state (J1 = -110 cm-1; J2 = -228 cm-1, g = 2.07). For pentanuclear clusters of type C in 4, the exchange model is based on a strongly antiferromagnetically coupled central linear trinuclear Cu 3 group (J1 = -125 cm-1) and two outer Cu centers weakly antiferromagnetically coupled to the terminal Cu ions of the triad (J2 = -12.5 cm-1). the Partner Organisations 2014.
