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Molbank, Volume 2020, Issue 1 (March 2020) – 23 articles

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Short Note
2,4,6-Tris(4-Iodophenyl)-1,3,5-trimethylbenzene
Molbank 2020, 2020(1), M1121; https://doi.org/10.3390/M1121 - 20 Mar 2020
Cited by 1 | Viewed by 1251
Abstract
2,4,6-Tris(4-iodophenyl)-1,3,5-trimethylbenzene was synthesized from 2,4,6-triphenyl-1,3,5-trimethylbenzene, using [bis(trifluoroacetoxy)iodo]benzene as the iodinating agent. The title compound was characterized by means of NMR, IR, and mass spectrometry, as well as TG analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
(E)-1,1,1-Trifluoro-6,6-bis(4-methoxyphenyl)hexa-3,5-dien-2-one
Molbank 2020, 2020(1), M1120; https://doi.org/10.3390/M1120 - 11 Mar 2020
Cited by 2 | Viewed by 943
Abstract
The title compound was obtained in high yield (84%) via the deacetylation of 3-(3,3-bis(4-methoxyphenyl)allylidene)-1,1,1,5,5,5-hexafluoro-2,4-pentanedione with K2CO3 in refluxing methanol. This previously unreported compound has been fully characterized by 19F{1H}, 1H and 13C{1H} NMR, IR, UV-Vis, and HRMS. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity
Molbank 2020, 2020(1), M1119; https://doi.org/10.3390/M1119 - 06 Mar 2020
Cited by 2 | Viewed by 1072
Abstract
3′,5′-O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2′-deoxyguanosine was synthesized from 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2′-deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2′-deoxyguanosine, however, failed to give [...] Read more.
3′,5′-O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2′-deoxyguanosine was synthesized from 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2′-deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3′,5′-O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2′-deoxyguanosine, however, failed to give the corresponding fluorinated product. It was found that 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine is labile under acidic conditions, but sufficiently stable in dichloroacetic acid used in solid phase synthesis. Incorporation of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis failed to give the desired products. Furthermore, treatment of 8-fluoro-N-2-isobutyryl-2′-deoxyguanosine with aqueous ammonium hydroxide did not give 8-fluoro-2′-deoxyguanosine, but led to the formation of a mixture consisting of 8-amino-N-2-isobutyryl-2′-deoxyguanosine and C8:5′-O-cyclo-2′-deoxyguanosine. Taken together, an alternative N-protecting group and possibly modified solid phase synthetic cycle conditions will be required for the incorporation of 8-fluoro-2′-deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Communication
6-Imino-1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1′,2′:1,2]imidazo[4,5-f]benzimidazole-13-one: Synthesis and Cytotoxicity Evaluation
Molbank 2020, 2020(1), M1118; https://doi.org/10.3390/M1118 - 05 Mar 2020
Cited by 2 | Viewed by 1218
Abstract
The first report of an iminoquinone of imidazo[4,5-f]benzimidazole is described. The 2D-NOESY spectrum of 1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1’,2’:1,2]imidazo[4,5-f]benzimidazol-6-amine was used to confirm the location of the imine moiety at the C-6 position of the title compound. Cytotoxicity data from the National Cancer Institute are included. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Short Note
Diethyl pyrrole-2,5-dicarboxylate
Molbank 2020, 2020(1), M1117; https://doi.org/10.3390/M1117 - 17 Feb 2020
Cited by 1 | Viewed by 1105
Abstract
The title compound was obtained in moderate yield by a new and unexpected base-induced ring contraction from a 1,4-thiazine precursor. Its X-ray structure showing hydrogen bonded dimers was compared with those of other crystallographically characterised 2-acylpyrroles. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Short Note
4-(2-Bromovinyl)benzocyclobutene
Molbank 2020, 2020(1), M1116; https://doi.org/10.3390/M1116 - 05 Feb 2020
Viewed by 1069
Abstract
4-(2-Bromovinyl)benzocyclobutene was prepared via a five stage synthesis starting from benzocyclobutene in an overall 30% yield. 4-(2-Bromovinyl)benzocyclobutene has a potential applications in synthesis of monomers for dielectric materials. Full article
(This article belongs to the Section Organic Synthesis)
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Editorial
Acknowledgement to Reviewers of Molbank in 2019
Molbank 2020, 2020(1), M1115; https://doi.org/10.3390/M1115 - 31 Jan 2020
Viewed by 909
Abstract
The editorial team greatly appreciates the reviewers who have dedicated their considerable time and expertise to the journal’s rigorous editorial process over the past 12 months, regardless of whether the papers are finally published or not [...] Full article
Communication
(E)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines
Molbank 2020, 2020(1), M1114; https://doi.org/10.3390/M1114 - 30 Jan 2020
Cited by 9 | Viewed by 1363
Abstract
(E)-1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid (2E,6E)-2,6-bis(3,4-dimethoxybenzylidene)acetone and ethyl hydrazinobenzoate in high yield and purity (>95% by High-performance liquid chromatography (HPLC)). The compound has been fully characterized by 1H, 13C [...] Read more.
(E)-1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid (2E,6E)-2,6-bis(3,4-dimethoxybenzylidene)acetone and ethyl hydrazinobenzoate in high yield and purity (>95% by High-performance liquid chromatography (HPLC)). The compound has been fully characterized by 1H, 13C NMR, FTIR, UV-Vis and HRMS and its activity was evaluated in terms of its potential interaction with DNA as well as its cytotoxicity against resistant and non-resistant tumor cells. Both DNA thermal denaturation and DNA viscosity measurements revealed that a significant intercalation binding takes place upon treatment of the DNA with the synthesized pyrazoline, causing an increase in melting temperature by 3.53 ± 0.11 °C and considerable DNA lengthening and viscosity increase. However, neither re-sensitisation of Doxorubicin (DO X)-resistant breast cancer and multidrug resistance (MDR) reversal nor synergistic activity with DOX by potentially increasing the DOX cell killing ability was observed. Full article
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Communication
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity
Molbank 2020, 2020(1), M1113; https://doi.org/10.3390/M1113 - 29 Jan 2020
Cited by 3 | Viewed by 1274
Abstract
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential [...] Read more.
1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells). Full article
(This article belongs to the Collection Heterocycle Reactions)
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Short Note
(22E,24S)-24-Propylcholest-5en-3α-acetate: A New Steroid from the Stembark Aglaia angustifolia (Miq.) (Meliaceae)
Molbank 2020, 2020(1), M1112; https://doi.org/10.3390/M1112 - 28 Jan 2020
Cited by 4 | Viewed by 1309
Abstract
A new propylcholesterol-type steroid, namely (22E,24S)-24-propylcholest-5en-3α-acetate (1), has been isolated from the stembark of Aglaia angustifolia (Miq.). The structure of 1 was determined on the basis of spectroscopic data including 1D- and 2D-NMR as well as high [...] Read more.
A new propylcholesterol-type steroid, namely (22E,24S)-24-propylcholest-5en-3α-acetate (1), has been isolated from the stembark of Aglaia angustifolia (Miq.). The structure of 1 was determined on the basis of spectroscopic data including 1D- and 2D-NMR as well as high resolution mass spectroscopy analysis. Compound 1 showed weak activity against the MCF-7 breast cancer cell line. Full article
(This article belongs to the Section Natural Products)
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Communication
Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block
Molbank 2020, 2020(1), M1111; https://doi.org/10.3390/M1111 - 18 Jan 2020
Cited by 1 | Viewed by 1134
Abstract
Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to [...] Read more.
Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to the diastereomeric sulfoxide products was achieved. The product was fully characterized by 1H, 13C and 2D NMR alongside MS analysis. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Communication
Half-Sandwich Arene-Osmium(II) Complexes with Phosphinite Ligands
Molbank 2020, 2020(1), M1110; https://doi.org/10.3390/M1110 - 17 Jan 2020
Cited by 1 | Viewed by 983
Abstract
The synthesis of a series of arene-osmium(II) complexes containing phosphinite-type ligands, namely, [OsCl2(η6-p-cymene){R2PO(CH2)nPh}] (R = Ph, n = 1 (4a), 2 (4b), 3 (4c); [...] Read more.
The synthesis of a series of arene-osmium(II) complexes containing phosphinite-type ligands, namely, [OsCl2(η6-p-cymene){R2PO(CH2)nPh}] (R = Ph, n = 1 (4a), 2 (4b), 3 (4c); R = iPr, n = 1 (5a), 2 (5b), 3 (5c)) and [OsCl2(η6-benzene){iPr2PO(CH2)2Ph}] (7), is presented. All these compounds were characterized by elemental analysis and multinuclear NMR spectroscopy (31P{1H}, 1H and 13C{1H}), and the structure of [OsCl2(η6-p-cymene){Ph2PO(CH2)3Ph}] (4c) unequivocally confirmed through a single-crystal X-ray diffraction study. Attempts to generate the tethered species [OsCl2{η6:κ1(P)-C6H5(CH2)nOPR2}] by intramolecular exchange of the coordinated arene in 4-5a-c or 7, upon thermal or MW heating, failed. Full article
(This article belongs to the Section Structure Determination)
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Short Note
2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide
Molbank 2020, 2020(1), M1109; https://doi.org/10.3390/M1109 - 14 Jan 2020
Viewed by 898
Abstract
2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide was synthesized (yield 50%) by a two-step procedure. The first step starts with a benzothiadiphosphole and bis-Grignard reagent, and the second step consists of adding the sodium salt of a derivative of cardanol. The structure of newly [...] Read more.
2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide was synthesized (yield 50%) by a two-step procedure. The first step starts with a benzothiadiphosphole and bis-Grignard reagent, and the second step consists of adding the sodium salt of a derivative of cardanol. The structure of newly synthesized compound was elucidated based on 1H-NMR, 13C-NMR, 31P-NMR, IR, Electron Spray Ionization (ESI)–MS, Gas Chromatography-Mass Spectroscopy (GC–MS), and Electron Spray Ionization-High Resolution Mass Spectroscopy (ESI–HRMS). Full article
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Communication
Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses
Molbank 2020, 2020(1), M1108; https://doi.org/10.3390/M1108 - 14 Jan 2020
Cited by 2 | Viewed by 1318
Abstract
During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation [...] Read more.
During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation of the pure epoxide was not possible since a rapid reversible conversion accompanied by the migration of the ester group took place and resulted in the formation of an unusual oxetane-bridged disaccharide scaffold. X-ray diffractometric structure elucidation and the suggested mechanism of the rearrangement are provided. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Communication
Dimethyl 2-{[2-(2-Methoxy-1-methoxycarbonyl-2-oxoethyl)-4,5,7-trimethoxy-3-(2,4,5-trimethoxyphenyl)-2,3-dihydro-1H-inden-1-yl]methyl}malonate
Molbank 2020, 2020(1), M1107; https://doi.org/10.3390/M1107 - 14 Jan 2020
Viewed by 1224
Abstract
A simple synthetic approach to dimethyl 2-{[2-(2-methoxy-1-methoxycarbonyl-2-oxoethyl)-4,5,7-trimethoxy-3-(2,4,5-trimethoxyphenyl)-2,3-dihydro-1H-inden-1-yl]methyl}malonate has been developed, based on a B(C6F5)3-induced domino dimerization of 2-(2,4,5-trimethoxyphenyl)cyclopropane-1,1-diester. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
2-(Bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-adamantan-2-ol
Molbank 2020, 2020(1), M1106; https://doi.org/10.3390/M1106 - 10 Jan 2020
Cited by 1 | Viewed by 1194
Abstract
A new adamantan-2-ol with a 2-bicyclo[4.2.0]octa-1,3,5-trien-3-yl substituent in the position 2 was synthesized via two stage synthesis starting from benzocyclobutene and adamatan-2-one. The structure of the title compound was determined using 1H-and 13C-NMR, HRMS and XRD. Full article
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Communication
(2Sp,4R,8Sp)-4-Methyl-1-phenyl-diferroceno-5-Z-ethylene-1-phosphinoxide
Molbank 2020, 2020(1), M1105; https://doi.org/10.3390/M1105 - 08 Jan 2020
Cited by 2 | Viewed by 1117
Abstract
We present a synthesis of the title compound, a homochiral diferroceno cycle intended for use in asymmetric catalysis. We present a hydrovinylation protocol, which allows the production of the title compound in two steps from a known diferrocenyl precursor. We obtained one of [...] Read more.
We present a synthesis of the title compound, a homochiral diferroceno cycle intended for use in asymmetric catalysis. We present a hydrovinylation protocol, which allows the production of the title compound in two steps from a known diferrocenyl precursor. We obtained one of two possible diastereomers selectively and propose a plausible regio- and stereoselective reaction mechanism. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
N′-Acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide
Molbank 2020, 2020(1), M1104; https://doi.org/10.3390/M1104 - 07 Jan 2020
Cited by 1 | Viewed by 1168
Abstract
Synthesis of N′-acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide from the phenyl acetates of 3-acetyl-5-(3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl in alkaline medium and its characterization by spectroscopic methods. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Short Note
2-Hydroxy-N′-(4-fluorobenzoyl)benzohydrazide
Molbank 2020, 2020(1), M1103; https://doi.org/10.3390/M1103 - 24 Dec 2019
Cited by 2 | Viewed by 2121
Abstract
2-Hydroxy-N′-(4-fluorobenzoyl)benzohydrazide was synthesized in two steps using methyl salicylate as the starting material. The reaction took place via microwave-aided hydrazinolysis, followed by acylation using 4-fluorobenzoyl chloride at low temperature to yield the target compound. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
Bicyclo[4.2.0]octa-1,3,5-trien-3-yl-dimethyl((E)-styryl)-silane
Molbank 2020, 2020(1), M1102; https://doi.org/10.3390/M1102 - 23 Dec 2019
Cited by 1 | Viewed by 1214
Abstract
Bicyclo[4.2.0]octa-1,3,5-trien-3-yl-dimethyl-((E)-styryl)-silane was synthesized via three stage synthesis starting from benzocyclobutene and (2-bromo-vinyl)-benzene. The structure of the product was determined using 1H- and 13C-NMR and HRMS. Full article
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Short Note
Bis(N′-(3-chlorobenzoyl)isonicotinohydrazide)iron(III) Complex
Molbank 2020, 2020(1), M1101; https://doi.org/10.3390/M1101 - 20 Dec 2019
Viewed by 1135
Abstract
The bis(N′-(3-chlorobenzoyl)isonicotinohydrazide)iron(III) complex was synthesised from N′-(3-chlorobenzoyl)isonicotinohydrazide and iron(III) metal by reflux in an ethanol solution. The title compound was characterised by Fourier-transform infrared spectroscopy (FTIR) spectroscopy, differential thermal analysis/thermogravimetric analysis (DTA/TGA) and UV-visible spectroscopy. The results indicate that coordination [...] Read more.
The bis(N′-(3-chlorobenzoyl)isonicotinohydrazide)iron(III) complex was synthesised from N′-(3-chlorobenzoyl)isonicotinohydrazide and iron(III) metal by reflux in an ethanol solution. The title compound was characterised by Fourier-transform infrared spectroscopy (FTIR) spectroscopy, differential thermal analysis/thermogravimetric analysis (DTA/TGA) and UV-visible spectroscopy. The results indicate that coordination of the iron(III) ion to the ligand increased its thermal stability. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

Communication
Synthesis of N-Heterocyclic Analogues of 28-O-Methyl Betulinate, and Their Antibacterial and Antifungal Properties
Molbank 2020, 2020(1), M1100; https://doi.org/10.3390/M1100 - 19 Dec 2019
Cited by 3 | Viewed by 1154
Abstract
The paper presents the results on the one-pot pyridine quaternization using betulinic 28-O-methyl ester (1) and Tempo+Br3 cation followed by reduction of the resulting salt (2) to 1,2,5,6-tetrahydropyridine derivative (3). The [...] Read more.
The paper presents the results on the one-pot pyridine quaternization using betulinic 28-O-methyl ester (1) and Tempo+Br3 cation followed by reduction of the resulting salt (2) to 1,2,5,6-tetrahydropyridine derivative (3). The structures of new compounds are confirmed by means of 1D and 2D-NMR spectroscopy, as well as MALDI TOF/TOF spectrometry. The derivatives 2 and 3 are active against S. aureus at the minimum inhibitory concentration (MIC) of 4 μg/mL and 16 μg/mL, correspondingly. Full article
(This article belongs to the Section Natural Products)
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Short Note
N-(2-Hydroxy-1,1-dimethylethyl)-3-methylbenzamide
Molbank 2020, 2020(1), M1099; https://doi.org/10.3390/M1099 - 19 Dec 2019
Cited by 5 | Viewed by 1152
Abstract
The title compound, N-(2-hydroxy-1,1-dimethylethyl)-3-methylbenzamide was synthesized by reacting 3-methylbenzoyl chloride or 3-methylbenzoic acid with 2-amino-2-methyl-1-propanol. In the present report, the synthesized target compound was fully characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS), its composition confirmed [...] Read more.
The title compound, N-(2-hydroxy-1,1-dimethylethyl)-3-methylbenzamide was synthesized by reacting 3-methylbenzoyl chloride or 3-methylbenzoic acid with 2-amino-2-methyl-1-propanol. In the present report, the synthesized target compound was fully characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS), its composition confirmed by elemental analysis, and its structure determined and confirmed by X-ray analysis. The importance of this compound lies in its possession of an N,O-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C–H bond functionalization reactions. Full article
(This article belongs to the Special Issue Molecules from Side Reactions)
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Figure 1

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