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Journal articles on the topic 'Bis-guanidine'

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Published: 4 June 2021

Last updated: 13 February 2022

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1

Strassl, Florian, Alexander Hoffmann, Benjamin Grimm-Lebsanft, Dieter Rukser, Florian Biebl, Mai Tran, Fabian Metz, Michael Rübhausen, and Sonja Herres-Pawlis. "Fluorescent Bis(guanidine) Copper Complexes as Precursors for Hydroxylation Catalysis." Inorganics 6, no. 4 (October 20, 2018): 114. http://dx.doi.org/10.3390/inorganics6040114.

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Bis(guanidine) copper complexes are known for their ability to activate dioxygen. Unfortunately, until now, no bis(guanidine) copper-dioxygen adduct has been able to transfer oxygen to substrates. Using an aromatic backbone, fluorescence properties can be added to the copper(I) complex which renders them useful for later reaction monitoring. The novel bis(guanidine) ligand DMEG2tol stabilizes copper(I) and copper(II) complexes (characterized by single crystal X-ray diffraction, IR spectroscopy, and mass spectrometry) and, after oxygen activation, bis(µ-oxido) dicopper(III) complexes which have been characterized by low-temperature UV/Vis and Raman spectroscopy. These bis(guanidine) stabilized bis(µ-oxido) complexes are able to mediate tyrosinase-like hydroxylation activity as first examples of bis(guanidine) stabilized complexes. The experimental study is accompanied by density functional theory calculations which highlight the special role of the different guanidine donors.

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2

Elmes, BC, G. Holan, GT Wernert, and DA Winkler. "The Synthesis of Bisguanidinoalkanes and Guanidinoalkanes, N- or N'-Substituted With Pyrimidines, as Analogues of Chlorhexidine." Australian Journal of Chemistry 49, no. 5 (1996): 573. http://dx.doi.org/10.1071/ch9960573.

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A series of N,N???- alkanediylbis [N?-(5-halopyrimidin-2-yl)guanidine] salts has been synthesized along with N,N???-(trans-cyclohexane-1,4-diyl) bis [N'-(5-chloropyrimidin-2-yl)guanidine], N,N???-(cis-cyclohexane-1,4-diyl) bis [N?-(5-chloropyrimidin-2-yl)guanidine] dihydrochloride and N-(cis-4-amino-cyclohexan-1-yl)-N'-(5-chloropyrimidin-2-yl)guanidine dihydrochloride . Furthermore, a series of N-(alkan-1-yl)-N?-(5-chloropyrimidin-2yl)guanidine hydrochlorides and N-(6-aminohexan-1-yl)-N?-(5-chloropyrimidin-2-yl)guanidine dihydrochloride were synthesized. This series of compounds was prepared by displacement reactions of 2-methylsulfonylpyrimidines with bisguanidinoalkanes or by condensation of 5-chloro-2-cyanoaminopyrimidine (5-chloropyrimidin-2-ylcyanamide) with alkylamines .

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3

Sudha, L., K. Subramanian, J. Senthil Selvan, Th Steiner, G. Koellner, K. Ramdas, and N. Srinivasan. "1,2-Bis(2,6-diethylphenyl)-3,3-(oxydiethyl)guanidine." Acta Crystallographica Section C Crystal Structure Communications 53, no. 1 (January 15, 1997): 88–90. http://dx.doi.org/10.1107/s0108270196011080.

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4

Rösch, Andreas, Simon H. F. Schreiner, Philipp Schüler, Helmar Görls, and Robert Kretschmer. "Magnesium bis(amidinate) and bis(guanidinate) complexes: impact of the ligand backbone and bridging groups on the coordination behaviour." Dalton Transactions 49, no. 37 (2020): 13072–82. http://dx.doi.org/10.1039/d0dt01923b.

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By dealing with various bis(amidine)s or bis(guanidine)s and different magnesium sources, we got a full house of homoleptic complexes. However, the joker card showing a heteroleptic complex is waiting to be used.

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5

Koskinen, Jere T. "Experimental and Computational Studies on Aminoguanidine Free Base, Monocation and Dication. Part III: Proton Affinities of Guanidine, Aminoguanidine and Glyoxal Bis(amidinohydrazone)." Zeitschrift für Naturforschung B 53, no. 3 (March 1, 1998): 386–92. http://dx.doi.org/10.1515/znb-1998-0320.

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Abstract The structures of glyoxal bis(amidinohydrazone) (GBG) free base and glyoxal bis(amidi-nohydrazonium) monocation and dication were calculated quantum chemically by using the density functional hybrid method B3-LYP with the standard basis set 6 -31 G (d). Proton affinities calculated from these data are 246.4 kcal/mol for the free base and 176.0 kcal/mol for the monocation. The proton affinities of guanidine free base (246.2 kcal/mol), aminoguanidine free base (242.9 kcal/mol), aminoguanidinium monocation (88.6 kcal/mol) were calculated for reference. The B3-LYP functional overestimates the proton affinities for all the species studied. For example, for guanidine the proton affinity at the M P2/6-31G (d) level is 238.3 kcal/mol, the experimental reference value being 233 kcal/mol. However, from the B3-LYP values it can be concluded that in the gas phase all the three bases are nearly equally basic. On the other hand, it is known that in aqueous solution guanidine is a much stronger base than aminoguanidine and glyoxal bis(amidinohydrazone). The results are discussed from the point of view of molecular size, shape and symmetry, and hydrogen bonding in solution.

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6

Li, Cai, Kwok-Wa Ip, Wai-Lun Man, Dan Song, Ming-Liang He, Shek-Man Yiu, Tai-Chu Lau, and Guangyu Zhu. "Cytotoxic (salen)ruthenium(iii) anticancer complexes exhibit different modes of cell death directed by axial ligands." Chemical Science 8, no. 10 (2017): 6865–70. http://dx.doi.org/10.1039/c7sc02205k.

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7

Wittmann, Harald, Andrea Schorm, and Jörg Sundermeyer. "Chelatliganden auf Basis peralkylierter Bis- und Tris-Guanidine." Zeitschrift für anorganische und allgemeine Chemie 626, no. 7 (July 2000): 1583–90. http://dx.doi.org/10.1002/1521-3749(200007)626:7<1583::aid-zaac1583>3.0.co;2-3.

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8

Said, Muhammad, Sadia Rehman, Muhammad Ikram, Hizbullah Khan, and Carola Schulzke. "Synthesis and crystal structure analyses of tri-substituted guanidine-based copper(II) complexes." Zeitschrift für Naturforschung B 76, no. 3-4 (March 22, 2021): 193–99. http://dx.doi.org/10.1515/znb-2020-0155.

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Abstract Three guanidine-derived tri-substituted ligands viz. N-pivaloyl-N′,N″-bis-(2-methoxyphenyl)guanidine (L1), N-pivaloyl-N′-(2-methoxyphenyl)-N″-phenylguanidine (L2) and N-pivaloyl-N′-(2-methoxyphenyl)-N″-(2-tolyl)guanidine (L3) were reacted with Cu(II) acetate to produce the corresponding complexes. The significance of the substituent on N″ for the resulting molecular structures and their packing in the solid state has been studied with respect to the structural specifics of the corresponding Cu(II) complexes. The key characteristic of the guanidine-based metal complexation with Cu(II) is the formation of an essentially square planar core with an N2O2 donor set. As an exception, in the complex of L1, the substituent’s methoxy moiety also interacts with the Cu(II) center to generate a square-pyramidal geometry. The hydroxyl groups of the imidic acid tautomeric forms of L1–L3, in addition to N″, are also bonded to Cu(II) in all three complexes rather than the nitrogen donor of the guanidine motif.

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9

Santos Vieira, Ines dos, and Sonja Herres-Pawlis. "Novel Guanidine-Quinoline Hybrid Ligands and the Application of their Zinc Complexes in Lactide Polymerisation." Zeitschrift für Naturforschung B 67, no. 4 (April 1, 2012): 320–30. http://dx.doi.org/10.1515/znb-2012-0405.

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The syntheses of the three new guanidine-quinoline hybrid ligands TMGmqu, DMEGmqu and TMGtbqu are reported. Zinc chlorido and triflato complexes with these ligands were obtained and structurally characterised by X-ray crystallography. In the chlorido complexes the zinc atom is coordinated by two chlorido ligands and the bidentate guanidine ligand in a distorted tetrahedron. Using zinc triflate, tetrahedral bis(chelate) complexes are formed, and the triflate anions serve only for charge compensation. All reported complexes show activity in the polymerisation of rac-lactide, with the chlorido complexes only showing a poor activity. With the bis(chelate) triflato complexes a high polymerisation activity with a slight heterotactic bias was observed. Kinetic studies reveal a firstorder chain growth reaction for the lactide polymerisation with all complexes.

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10

Singh, Prabal, S. Yugandar, S. Kumar, H. Ila, and H. Junjappa. "Synthesis of Novel Five- and Six-Membered Ferrocene-Containing Heterocycles and Heteroaromatics via Cyclocondensation of 1-Ferrocenyl-3,3-bis(methylthio)prop-2-en-1-one with Various Bifunctional Nucleophiles." Synthesis 49, no. 12 (March 10, 2017): 2700–2710. http://dx.doi.org/10.1055/s-0036-1588966.

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Synthesis and reactions of 1-ferrocenyl-3,3-bis(methylthio)prop-2-en-1-one as a versatile 1,3-bielectrophilic synthon leading to a range of novel ferrocene-containing five- and six-membered heterocycles and heteroaromatics has been reported. Thus its cyclocondensation with various bifunctional heteronucleophiles, such as hydrazine, phenylhydrazine, hydroxylamine, guanidine, and amidine, affords a range of ferrocene-substituted pyrazoles, oxazoles, and pyrimidines in highly regioselective manner. Synthesis of few ferrocenyl-substituted pyridines and thiophenes has also been described. Similarly cycloaromatization of this ferrocene-substituted α-oxoketene dithioacetal with anions generated from (het)arylacetonitriles provides a facile entry to ferrocene-substituted heteroaromatics in good yields. Synthesis of a few 2-ferrocenylvinyl-substituted heterocycles, such as pyrazoles, isoxazoles, and pyrimidines, via cyclocondensation of a novel 5-ferrocenyl-1,1-bis(methylthio)penta-1,4-dien-3-one with phenylhydrazine, hydroxylamine, and guanidine has also been reported.

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11

Zhou, Hui, Wei Chen, Ji-Hong Liu, Wen-Zhen Zhang, and Xiao-Bing Lu. "Highly effective capture and subsequent catalytic transformation of low-concentration CO2 by superbasic guanidines." Green Chemistry 22, no. 22 (2020): 7832–38. http://dx.doi.org/10.1039/d0gc03009k.

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We have developed a novel N,N′-bis(imidazolyl)guanidine-based system, which shows high performance in low-concentration CO₂ capture and subsequent catalytic transformation to functionalized (4E,5Z)-4-imino-5-benzylideneoxazolidine-2-ones.

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12

Oakley, Sarah H., Martyn P. Coles, and Peter B. Hitchcock. "Structural and Catalytic Properties of Bis(guanidine)copper(I) Halides." Inorganic Chemistry 42, no. 10 (May 2003): 3154–56. http://dx.doi.org/10.1021/ic034213b.

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13

Börner, Janna, Sonja Herres-Pawlis, Ulrich Flörke, and Klaus Huber. "[Bis(guanidine)]zinc Complexes and Their Application in Lactide Polymerisation." European Journal of Inorganic Chemistry 2007, no. 36 (December 2007): 5645–51. http://dx.doi.org/10.1002/ejic.200700894.

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14

Herres-Pawlis, Sonja, Ulrich Flörke, and Gerald Henkel. "Tuning of Copper(I)-Dioxygen Reactivity by Bis(guanidine) Ligands." European Journal of Inorganic Chemistry 2005, no. 19 (October 2005): 3815–24. http://dx.doi.org/10.1002/ejic.200400822.

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15

Phan, Chin-Soon, Kenichi Matsuda, Nandani Balloo, Kei Fujita, Toshiyuki Wakimoto, and Tatsufumi Okino. "Argicyclamides A–C Unveil Enzymatic Basis for Guanidine Bis-prenylation." Journal of the American Chemical Society 143, no. 27 (June 28, 2021): 10083–87. http://dx.doi.org/10.1021/jacs.1c05732.

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16

Strassl, Florian, Benjamin Grimm-Lebsanft, Dieter Rukser, Florian Biebl, Mykola Biednov, Calvin Brett, Riccardo Timmermann, et al. "Oxygen Activation by Copper Complexes with an Aromatic Bis(guanidine) Ligand." European Journal of Inorganic Chemistry 2017, no. 27 (July 21, 2017): 3350–59. http://dx.doi.org/10.1002/ejic.201700528.

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17

Wang, Mengwei, Yunling Li, Zhifang Wu, Jun Li, and Zhifei Wang. "Synthesis and Surface Activity of N‐coco Propylene Bis‐guanidine Hydrochloride." ChemistrySelect 4, no. 35 (September 19, 2019): 10601–8. http://dx.doi.org/10.1002/slct.201902116.

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18

Kantlehner, Willi, Ioannis Tiritiris, Markus Vettel, and Wolfgang Frey. "Orthoamide und Iminiumsalze, IIC. Darstellung von N-(ω-Ammonioalkyl)-N,N′,N′,N″,N″-peralkylierten Guanidiniumsalzen und N-(ω-Aminoalkyl)-N′,N′,N″,N″-tetramethylguanidinen." Zeitschrift für Naturforschung B 75, no. 6-7 (August 27, 2020): 665–84. http://dx.doi.org/10.1515/znb-2019-0229.

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AbstractN,N,N′,N′-Tetraalkylchlorformamidiniumchlorides 1a, b react with ω-dimethylaminoalkylamines 19, 20 to give mixtures of N-(ω-dimethylammonioalkyl)-guanidinium salts 12, 13 and N-(ω-dimethylaminoalkyl)-guanidinium salts 21, 22. These mixtures are transformed to mixtures of the ureas 15, 17 and N-(ω-dimethylaminoalkyl)-guanidines 23, 25 on treatment with aqueous sodium hydroxide. The reaction of N-(3-dimethylammoniopropyl)-guanidin 25a with dimethylsulfate in a molar ratio of 1:1 delivers a mixture of the N-(3-dimethylaminopropyl)-N,N,N′,N′,N″,N″-pentamethyl-guanidinium salt 29a and the N-(3-dimethylammoniopropyl)-N,N′,N′,N″,N″-pentamethyl-guanidinium-bis (methylsulfate) 33a. The action of dimethylsulfate on the guanidines 23a, 25a in a molar ratio of 2:1 affords the bisquarternary salts 32a, 33a. Alkylating reagents as methyliodide, benzylbromide, allylbromide and chloroacetonitrile attack N-(2-dimethylaminoethyl)-N′,N′,N″,N″-tetraethylguanidine (23b) in a molar ratio of 1:1 cleanly at the dimethylaminoethylgroup to give the ammonium salts 30a–d. As a strong base the guanidine 23b dehydrochlorinates β-Chlorpropionitrile and chloroacetone under formation of the guanidinium salt 21c. In contrast to this the reaction of ethyl bromoacetate with the N-(2-dimethylaminoethyl)guanidine 23b occurs at the guanidinogroup giving the guanidinium salt 28c. The methylation of the guanidinium chlorides 21a, 22a with dimethyl sulfate affords the bis-quaternary salts 35b, 36b with mixed anions. From the heterocyclic guanidines 14, 16 and the alkylating reagents benzylbromide and ethyl bromoacetate the heterocyclic guanidinium salts 37a, b, 39a, b can be obtained. The reactions with ethyl chloroformiate proceed in an analogous way giving the guanidinium salts 37c, 39c. The N-alkyl-N,N,N′,N′-tetramethyl-(3-ureidopropyl)guanidinium salts 41a, b can be prepared from the N′,N′,N″,N″-tetramethyl-N′′-(3-ureidopropyl) guanidine 17a and the alkylating compounds dimethyl sulfate and benzyl bromide. Several compounds obtained that way were transformed to the corresponding tetraphenyloborates and bis(tetraphenylborates), respectively.

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19

Perry, David, Bracken Roberts, Ginamarie Debevec, Heather Michaels, Debopam Chakrabarti, and Adel Nefzi. "Identification of Bis-Cyclic Guanidines as Antiplasmodial Compounds from Positional Scanning Mixture-Based Libraries." Molecules 24, no. 6 (March 20, 2019): 1100. http://dx.doi.org/10.3390/molecules24061100.

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The screening of more than 30 million compounds derived from 81 small molecule libraries built on 81 distinct scaffolds identified pyrrolidine bis-cyclic guanidine library (TPI-1955) to be one of the most active and selective antiplasmodial libraries. The screening of the positional scanning library TPI-1955 arranged on four sets of sublibraries (26 + 26 + 26 + 40), totaling 120 samples for testing provided information about the most important groups of each variable position in the TPI-1955 library containing 738,192 unique compounds. The parallel synthesis of the individual compounds derived from the deconvolution of the positional scanning library led to the identification of active selective antiplasmodial pyrrolidine bis-cyclic guanidines.

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20

Meenongwa, Atittaya, Unchulee Chaveerach, and Alexander J. Blake. "Methanol[1-(methoxymethanimidoyl)-2-(pyridin-2-ylmethyl)guanidine]bis(perchlorato)copper(II)." Acta Crystallographica Section C Crystal Structure Communications 68, no. 6 (May 6, 2012): m143—m146. http://dx.doi.org/10.1107/s0108270112015843.

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The title complex, [Cu(ClO4)2(C9H13N5O)(CH3OH)], was synthesized from a methanolysis reaction ofN-(methylpyridin-2-yl)cyanoguanidine (L3) and copper(II) perchlorate hexahydrate in a 1:1 molar ratio. The CuIIion is six-coordinated by an N3O3donor set which confers a highly distorted and asymmetric octahedral geometry. Three N-donor atoms from the chelating 1-(methoxymethanimidoyl)-2-(pyridin-2-ylmethyl)guanidine (L3m) ligand and one O atom from the methanol molecule define the equatorial plane, with two perchlorate O atoms in the apical sites, one of which has a long Cu—O bond of 2.9074 (19) Å. The dihedral angle between the five- and six-membered chelate rings is 8.21 (8)°. Two molecules are associated into a dimeric unit by intermolecular N—H...O(perchlorate) hydrogen bonds. Additionally, the weakly coordinated perchlorate anions also link adjacent [Cu(ClO4)2(L3m)(CH3OH)] dimers by hydrogen-bonding interactions, resulting in a two-dimensional layer in the (100) plane. Further C—H...O hydrogen bonds link the two-dimensional layers along [100] to generate a three-dimensional network.

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21

Margetić, Davor, Tsutomu Ishikawa, and Takuya Kumamoto. "Exceptional Superbasicity of Bis(guanidine) Proton Sponges Imposed by the Bis(secododecahedrane) Molecular Scaffold: A Computational Study." European Journal of Organic Chemistry 2010, no. 34 (October 11, 2010): 6563–72. http://dx.doi.org/10.1002/ejoc.201000828.

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22

Ali, Sayyad, Muhammad Hassham Hassan Bin Asad, Fahad Khan, Ghulam Murtaza, Albert A. Rizvanov, Jamshed Iqbal, Borhan Babak, and Izhar Hussain. "Biological Evaluation of Newly Synthesized Biaryl Guanidine Derivatives to Arrest β-Secretase Enzymatic Activity Involved in Alzheimer’s Disease." BioMed Research International 2020 (May 11, 2020): 1–11. http://dx.doi.org/10.1155/2020/8934289.

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Proteases BACE1 (β-secretases) enzymes have been recognized as a promising target associated with Alzheimer’s disease (AD). This study was carried out on the principles of molecular docking, chemical synthesis, and enzymatic inhibition of BACE1 enzymes via biaryl guanidine-based ligands. Based on virtual screening, thirteen different compounds were synthesized and subsequently evaluated via in vitro and in vivo studies. Among them, 1,3-bis(5,6-difluoropyridin-3-yl)guanidine (compound (9)) was found the most potent (IC50=97±0.91 nM) and active to arrest (99%) β-secretase enzymes (FRET assay). Furthermore, it was found to improve the novel object recognition test and Morris water maze test significantly (p<0.05). Improved pharmacokinetic parameters, viz., Log Po/w (1.76), Log S (-2.73), and better penetration to the brain (BBB permeation) with zero Lipinski violation, made it possible to hit the BACE1 as a potential therapeutic source for AD.

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23

Erwin, B. G., and A. E. Pegg. "Regulation of spermidine/spermine N1-acetyltransferase in L6 cells by polyamines and related compounds." Biochemical Journal 238, no. 2 (September 1, 1986): 581–87. http://dx.doi.org/10.1042/bj2380581.

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Exposure of rat L6 cells in culture to exogenous polyamines led to a very large increase in the activity of spermidine/spermine N1-acetyltransferase. Spermine was more potent than spermidine in bringing about this increase, but in both cases the elevated acetyltransferase activity increased the cellular conversion of spermidine into putrescine. The N1-acetyltransferase turned over very rapidly in the L6 cells, with a half-life of 9 min after spermidine and 18 min after spermine. A wide variety of synthetic polyamine analogues also brought about a substantial induction of spermidine/spermine N1-acetyltransferase activity. These included sym-norspermidine, sym-norspermine, sym-homospermidine, N4-substituted spermidine derivatives, 1,3,6-triaminohexane, 1,4,7-triaminoheptane and deoxyspergualin, which were comparable with spermidine in their potency, and N1N8-bis(ethyl)spermidine, N1N9-bis(ethyl)homospermidine, methylglyoxal bis(guanylhydrazone), ethylglyoxal bis(guanylhydrazone) and 1,1′-[(methylethanediylidene)dinitrilo]bis(3-amino-guanidine), which were even more active than spermidine. It is suggested that these polyamine analogues may bring about a decrease in cellular polyamines not only by inhibiting biosynthesis but by stimulating the degradation of spermidine into putrescine.

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24

Vass, Valentin, Maximilian Dehmel, Florian Lehni, and Robert Kretschmer. "A Facile One-Pot Synthesis of 1,2,3-Tri- and 1,1,2,3-Tetrasubstituted Bis(guanidine)s from Bis(thiourea)s." European Journal of Organic Chemistry 2017, no. 34 (September 13, 2017): 5066–73. http://dx.doi.org/10.1002/ejoc.201700782.

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25

Begley, M. J., P. Hubberstey, P. H. Spittle, and P. H. Walton. "Structure of tetrakis(μ-acetato-5κO:κO')-bis(2-cyano-κN-guanidine)dicopper(II)." Acta Crystallographica Section C Crystal Structure Communications 49, no. 6 (June 15, 1993): 1047–49. http://dx.doi.org/10.1107/s0108270192005122.

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26

Herres-Pawlis, Sonja, Adam Neuba, Oliver Seewald, Tarimala Seshadri, Hans Egold, Ulrich Flörke, and Gerald Henkel. "A Library of Peralkylated Bis-guanidine Ligands for Use in Biomimetic Coordination Chemistry." European Journal of Organic Chemistry 2005, no. 22 (November 2005): 4879–90. http://dx.doi.org/10.1002/ejoc.200500340.

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27

Boeré, Robyn E., René T. Boeré, Jason Masuda, and Gotthelf Wolmershäuser. "Preparation, X-ray structure, and dynamic solution behaviour of N,N',N''-tris(2,6-diisopropylphenyl)- guanidine, and its reaction with molybdenum carbonyl." Canadian Journal of Chemistry 78, no. 12 (December 1, 2000): 1613–19. http://dx.doi.org/10.1139/v00-142.

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The reaction of N,N'-bis(2,6-diisopropylphenyl)carbodiimide with lithium 2,6-diisopropylanilide, quenching with water and recrystallization from heptane produces the symmetric guanidine [DipNH]2C=NDip which crystallizes in the triclinic system, space group P[Formula: see text], a = 10.6513(11), b = 10.8997(11), c = 16.2961(17) Å, α = 80.524(12), β = 78.921(13), γ = 70.060(12)°, V = 1735.2(3) Å3, Z = 2. The molecule crystallizes with three perpendicular 2,6-diisopropylphenyl groups, which surround and shield the central CN3 unit, and provide (almost) three-fold symmetry around the central atom. Its dynamic solution behaviour has been studied by VT NMR between -90 and +180°C, and is consistent with three distinct barriers to N-CAr rotation. Preliminary estimates of the Gibbs free energy of activation for the lower two barriers are 56 ± 2 and 73 ± 2 kJ mol1. Reaction of the title compound with Mo(CO)6 in refluxing n-heptane produces [DipNH]2C=NDip·Mo(CO)3, a complex in which Mo(CO)3 is η6-coordinated to one of the diisopropylphenyl rings.Key words: crystal structure, diisopropylaniline, guanidine, bulky ligands.

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28

Dagley, IJ, and JL Flippenanderson. "Synthesis of Cyclic Nitramines From Products of the Cyclocondensation Reaction of Guanidine With 2,3,5,6-Tetrahydroxypiperazine-1,4-dicarbaldehyde." Australian Journal of Chemistry 47, no. 11 (1994): 2033. http://dx.doi.org/10.1071/ch9942033.

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The reaction of 2,3,5,6-tetrahydroxypiperazine-1,4-dicarbaldehyde (1) with guanidine hydrochloride in hydrochloric acid can be controlled to give 2,6-diiminododecahydrodiimidazo[4,5-b:4′,5′-e] pyrazine (2a) or the cis isomer of 4,5-diamino-2-iminoimidazolidine (4). Compound (4) reacts with formaldehyde, or formic acid followed by reduction, to give 2-iminooctahydroimidazo[4,5-d] imidazole (7). Treatment of (2a) or (7) with nitric acid gives dinitro derivatives that were isolated as nitric acid salts of the cyclic guanidines. Reaction of the dinitro derivatives with nitric acid/acetic anhydride in the presence of chloride ion gives 4,8-dinitro-2,6-bis( nitroimino ) dodecahydrodiimidazo -[4,5-b:4′,5′-e] pyrazine (3a) and 1,3-dinitro-5-( nitroimino ) octahydroimidazo [4,5-d] imidazole (9). The reaction of (7) with nitric acid/ trifluoroacetic anhydride was controlled to give either the tetranitro or a dinitro bis ( trifluoroacetyl ) derivative of the corresponding bicyclic urea.

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29

Wang, Lei, and Bing-Tian Tu. "Electronic structure and optical properties of phosphate bis-guanidinoacetate crystal containing guanidine phosphate interaction." Acta Physica Sinica 68, no. 6 (2019): 064210. http://dx.doi.org/10.7498/aps.68.20181627.

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30

Herres, Sonja, Ulrich Flörke, and Gerald Henkel. "The first di-μ-hydroxo-bridged binuclear copper complex containing a bis-guanidine ligand." Acta Crystallographica Section C Crystal Structure Communications 60, no. 12 (November 23, 2004): m659—m660. http://dx.doi.org/10.1107/s0108270104023832.

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Song, Yongbo, Yulan Niu, Hongyan Zheng, and Ying Yao. "Interaction of Bis-Guanidinium Acetates Surfactants with Bovine Serum Albumin Evaluated by Spectroscopy." Tenside Surfactants Detergents 58, no. 3 (May 1, 2021): 187–94. http://dx.doi.org/10.1515/tsd-2020-2283.

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Abstract The interactions between cocopropane bis-guanidinium acetates, tallowpropane bis-guanidinium acetates with bovine serum albumin (BSA) in an aqueous solution were studied by fluorescence and circular dichroic spectroscopy measurements. The aim of the study was to elucidate the influence of the hydrophilic group and the length of the hydrophobic chain of these surfactants on the mechanism of binding to BSA. The results revealed that for both surfactants, at low concentrations, the Stern–Volmer plots had an upward curvature and at high concentrations, the quenching efficiency was decreased with increase in surfactant concentration. Different thermodynamics parameters demonstrated the existence of hydrogen bond and van der Waals force which acting as binding forces. Static quenching was observed among the protein and surfactant. The conformation of BSA was changed at higher surfactant concentrations as shown by synchronous fluorescence and CD spectroscopy. This work reveals the mechanism and binding characteristics between guanidine surfactants and protein, and provided the basis for further applications of surfactants.

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El-Demerdash, Amr, Céline Moriou, Marie-Thérèse Martin, Sylvain Petek, Cécile Debitus, and Ali Al-Mourabit. "Unguiculins A-C: cytotoxic bis-guanidine alkaloids from the French Polynesian sponge, Monanchora n. sp." Natural Product Research 32, no. 13 (October 25, 2017): 1512–17. http://dx.doi.org/10.1080/14786419.2017.1385011.

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Herrmann, Hendrik, Petra Walter, Elisabeth Kaifer, and Hans-Jörg Himmel. "Incorporation of a Redox-Active Bis(guanidine) in Low-Dimensional Tin and Lead Iodide Structures." European Journal of Inorganic Chemistry 2017, no. 47 (November 28, 2017): 5537. http://dx.doi.org/10.1002/ejic.201701351.

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Herrmann, Hendrik, Petra Walter, Elisabeth Kaifer, and Hans-Jörg Himmel. "Incorporation of a Redox-Active Bis(guanidine) in Low-Dimensional Tin and Lead Iodide Structures." European Journal of Inorganic Chemistry 2017, no. 47 (October 13, 2017): 5539–44. http://dx.doi.org/10.1002/ejic.201700840.

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Ceramella, Jessica, Annaluisa Mariconda, Camillo Rosano, Domenico Iacopetta, Anna Caruso, Pasquale Longo, Maria Stefania Sinicropi, and Carmela Saturnino. "α–ω Alkenyl‐bis‐ S ‐Guanidine Thiourea Dihydrobromide Affects HeLa Cell Growth Hampering Tubulin Polymerization." ChemMedChem 15, no. 23 (September 18, 2020): 2306–16. http://dx.doi.org/10.1002/cmdc.202000544.

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36

Coles, Martyn P., Steven F. Lee, Sarah H. Oakley, Guillermina Estiu, and Peter B. Hitchcock. "Nucleophilic activity of a linked bis{guanidine} leading to formation of a dicationic C4N4-heterocycle." Organic & Biomolecular Chemistry 5, no. 24 (2007): 3909. http://dx.doi.org/10.1039/b715209d.

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37

Li, Jun, Yunling Li, Zhifei Wang, Lu Zhang, Yajie Jiang, Wei Zhang, and Junli Wu. "Properties of Mixed System of N‐Coco Propylene Bis‐guanidine Acetate (CPGA) and Nonionic Surfactants." ChemistrySelect 6, no. 32 (August 23, 2021): 8205–12. http://dx.doi.org/10.1002/slct.202102335.

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Paul, Melanie, Alexander Hoffmann, and Sonja Herres-Pawlis. "Room temperature stable multitalent: highly reactive and versatile copper guanidine complexes in oxygenation reactions." JBIC Journal of Biological Inorganic Chemistry 26, no. 2-3 (February 17, 2021): 249–63. http://dx.doi.org/10.1007/s00775-021-01849-9.

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AbstractInspired by the efficiency of natural enzymes in organic transformation reactions, the development of synthetic catalysts for oxygenation and oxidation reactions under mild conditions still remains challenging. Tyrosinases serve as archetype when it comes to hydroxylation reactions involving molecular oxygen. We herein present new copper(I) guanidine halide complexes, capable of the activation of molecular oxygen at room temperature. The formation of the reactive bis(µ-oxido) dicopper(III) species and the influence of the anion are investigated by UV/Vis spectroscopy, mass spectrometry, and density functional theory. We highlight the catalytic hydroxylation activity towards diverse polycyclic aromatic alcohols under mild reaction conditions. The selective formation of reactive quinones provides a promising tool to design phenazine derivatives for medical applications. Graphic abstract

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Herres-Pawlis, Sonja, Roxana Haase, Pratik Verma, Alexander Hoffmann, Peng Kang, and T. Daniel P. Stack. "Formation of Hybrid Guanidine-Stabilized Bis(μ-oxo)dicopper Cores in Solution: Electronic and Steric Perturbations." European Journal of Inorganic Chemistry 2015, no. 32 (October 22, 2015): 5426–36. http://dx.doi.org/10.1002/ejic.201500884.

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Herres-Pawlis, Sonja, Pratik Verma, Roxana Haase, Peng Kang, Christopher T. Lyons, Erik C. Wasinger, Ulrich Flörke, Gerald Henkel, and T. Daniel P. Stack. "Phenolate Hydroxylation in a Bis(μ-oxo)dicopper(III) Complex: Lessons from the Guanidine/Amine Series." Journal of the American Chemical Society 131, no. 3 (January 28, 2009): 1154–69. http://dx.doi.org/10.1021/ja807809x.

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Osadchuk, Irina, Nele Konrad, Khai-Nghi Truong, Kari Rissanen, Eric Clot, Riina Aav, Dzmitry Kananovich, and Victor Borovkov. "Supramolecular Chirogenesis in Bis-Porphyrin: Crystallographic Structure and CD Spectra for a Complex with a Chiral Guanidine Derivative." Symmetry 13, no. 2 (February 5, 2021): 275. http://dx.doi.org/10.3390/sym13020275.

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The complexation of (3aR,7aR)-N-(3,5-bis(trifluoromethyl)phenyl)octahydro-2H-benzo[d]imidazol-2-imine (BTI), as a guest, to ethane-bridged bis(zinc octaethylporphyrin), bis(ZnOEP), as a host, has been studied by means of ultraviolet-visible (UV-Vis) and circular dichroism (CD) absorption spectroscopies, single crystal X-ray diffraction, and computational simulation. The formation of 1:2 host-guest complex was established by X-ray diffraction and UV-Vis titration studies. Two guest BTI molecules are located at the opposite sides of two porphyrin subunits of bis(ZnOEP) host, which is resting in the anti-conformation. The complexation of BTI molecules proceed via coordination of the imine nitrogens to the zinc ions of each porphyrin subunit of the host. Such supramolecular organization of the complex results in a screw arrangement of the two porphyrin subunits, inducing a strong CD signal in the Soret (B) band region. The corresponding DFT computational studies are in a good agreement with the experimental results and prove the presence of 1:2 host-guest complex as the major component in the solution (97.7%), but its optimized geometry differs from that observed in the solid-state. The UV-Vis and CD spectra simulated by using the solution-state geometry and the TD-DFT/ωB97X-D/cc-pVDZ + SMD (CH2Cl2) level of theory reproduced the experimentally obtained UV-Vis and CD spectra and confirmed the difference between the solid-state and solution structures. Moreover, it was shown that CD spectrum is very sensitive to the spatial arrangement of porphyrin subunits.

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Beyer, Lothar, Rainer Richter, Robert Wolf, Jana Zaumseil, Maria Lino-Pacheco, and Jorge Angulo-Cornejo. "Synthesis and molecular structure of bis(2-benzoylimino-benzimidazolinato)copper(II)-dimethylformamide — a metal-containing guanidine derivative." Inorganic Chemistry Communications 2, no. 5 (May 1999): 184–87. http://dx.doi.org/10.1016/s1387-7003(99)00043-x.

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43

Yeagley, Andrew A., Zhaoming Su, Kára D. McCullough, Roberta J. Worthington, and Christian Melander. "N-Substituted 2-aminoimidazoleinhibitors of MRSA biofilm formation accessed through direct 1,3-bis(tert-butoxycarbonyl)guanidine cyclization." Org. Biomol. Chem. 11, no. 1 (2013): 130–37. http://dx.doi.org/10.1039/c2ob26469b.

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44

Cong, Zhang, Chen Xiang, Hu Yongpeng, Bai Yang, Guo Zhaoqi, Fan Daidi, and Ma Haixia. "A series of guanidine salts of 3,6-bis-nitroguanyl-1,2,4,5-tetrazine: green nitrogen-rich gas-generating agent." RSC Advances 10, no. 60 (2020): 36287–94. http://dx.doi.org/10.1039/d0ra06766k.

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45

Bienemann, Olga, Roxana Haase, Ulrich Flörke, Artjom Döring, Dirk Kuckling, and Sonja Herres-Pawlis. "Neue Bisguanidin-Kupfer-Komplexe und ihre Anwendung in der ATRP/ New Bisguanidine-Copper Complexes and their Application in ATRP." Zeitschrift für Naturforschung B 65, no. 7 (July 1, 2010): 798–806. http://dx.doi.org/10.1515/znb-2010-0705.

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The ligands TMG2e [bis(N,N,N´,N´-tetramethylguanidino)ethane] and DMEG2e [N1,N2-bis(1,3-dimethylimidazolin-2-ylidene)ethane-1,2-diamine] were used in the complexation of copper cations to give the new complexes [Cu(TMG2e)2][Cu2I4], [Cu(TMG2e)Cl2] and [Cu(DMEG2e)2]-[CuCl2]. Single-crystal structure determination shows that the complexes [Cu(TMG2e)Cl2] and [Cu(DMEG2e)2][CuCl2] both crystallise in the monoclinic space group C2/c, the complex [Cu(TMG2e)2][Cu2I4] in the orthorhombic space group Pbca. The copper atoms in all complex cations reside in a coordination environment between tetrahedral and square-planar geometry. The application of copper complexes with TMG2e and DMEG2e as ligands in atom transfer radical polymerisation (ATRP) was investigated with styrene as monomer. The polymerisation process with both ligand systems shows even at low temperature unexpected high conversions and molecular weight distributions that are evidence of a well controlled ATRP. These first results in the application of guanidine ligands in ATRP show that these ligands have high potential, but that further process optimisations and ligand tuning are necessary to develop highly active catalysts for ATRP.

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Chen, Chun-Yen, Hui-Chang Lin, Yu-Ying Huang, Kun-Lung Chen, Jiann-Jyh Huang, Mou-Yung Yeh, and Fung Fuh Wong. "ChemInform Abstract: “One-Flask” Transformation of Isocyanates and Isothiocyanates to Guanidine Hydrochlorides by Using Sodium Bis(trimethylsilyl)amide." ChemInform 41, no. 27 (June 10, 2010): no. http://dx.doi.org/10.1002/chin.201027082.

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Hoffmann, Alexander, Janna Börner, Ulrich Flörke, and Sonja Herres-Pawlis. "Synthesis and properties of guanidine-pyridine hybridligands and structural characterisation of their mono- and bis(chelated) cobalt complexes." Inorganica Chimica Acta 362, no. 4 (March 2009): 1185–93. http://dx.doi.org/10.1016/j.ica.2008.06.002.

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Haase, Roxana, Tanja Beschnitt, Ulrich Flörke, and Sonja Herres-Pawlis. "Bidentate guanidine ligands with ethylene spacer in copper-dioxygen chemistry: Structural characterization of bis(μ-hydroxo) dicopper complexes." Inorganica Chimica Acta 374, no. 1 (August 2011): 546–57. http://dx.doi.org/10.1016/j.ica.2011.02.061.

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Tran, Minh Quan, Ludmila Ermolenko, Pascal Retailleau, Thanh Binh Nguyen, and Ali Al-Mourabit. "Reaction of Quinones and Guanidine Derivatives: Simple Access to Bis-2-aminobenzimidazole Moiety of Benzosceptrin and Other Benzazole Motifs." Organic Letters 16, no. 3 (January 30, 2014): 920–23. http://dx.doi.org/10.1021/ol403672p.

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Wang, Lei, Meixia Xiao, and Danghui Wang. "Single crystal structure, hydrogen bonding interaction, charge transfer and thermal properties of a new guanidine derivative crystal: Phosphate bis-guanidinoacetate." Journal of Molecular Structure 1195 (November 2019): 883–90. http://dx.doi.org/10.1016/j.molstruc.2019.06.036.

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