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- Volume 19, Issue 1, 2022
Current Organic Synthesis - Volume 19, Issue 1, 2022
Volume 19, Issue 1, 2022
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Facile Synthetic Protocols for the Preparation of New Impurities in Pemetrexed Disodium Heptahydrate as an Anti-cancer Drug
A facile synthetic protocol was employed to prepare process-related impurities associated with the synthesis of pemetrexed disodium heptahydrate, Alimta. The research work is described for the development of the novel synthetic methods and their structure elucidation of Pemetrexed glutamide, N-methyl pemetrexed, and N-methyl pemetrexed glutamide impurities. The listed impurities were deduced through spectral analysis, such as 1H-NMR, 13CNMR, and HRMS. The target compounds can be used as the reference substances for quality control.
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Isolation, Characterization, and Docking Studies of (Z)-Isopropyl 7-((1R, 2R, 3R, 5S)- 2-((1E, 3Z)-3-Fluoro-4-Phenoxybuta-1, 3-Dienyl)-3,5-Dihydroxycyclopentyl) Hept-5- Enoate, an Impurity of Tafluprost
Introduction: The origin, isolation, and characterization of (Z)-isopropyl 7-((1R, 2R, 3R, 5S)-2-((1E, 3Z)-3-fluoro-4-phenoxybuta-1, 3-dienyl)-3, 5-dihydroxycyclopentyl) hept-5-enoate, an impurity found in the preparation of an anti-glaucoma agent-Tafluprost has been described in this study. Materials and Methods: Further, an enantiospecific synthesis of (Z)-isopropyl 7-((1R, 2R, 3R, 5S)-2-((1E, 3Z)- 3-fluoro-4-phenoxybuta-1, 3-dienyl)-3, 5-dihydroxycyclopentyl) hept-5-enoate has been revealed using deoxofluorination as a key transformation of the strategy. Results and Discussions: Moreover, the impurity showing anti-glaucoma properties in docking studies with respect to bimatoprost has been described. Conclusion: The extention of our work towards docking studies and the present impurity molecule showed almost the same biological activity with respect to Tafluprost.
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Recent Developments in Arylation of N-Nucleophiles via Chan-Lam Reaction: Updates from 2012 Onwards
Authors: Fahimeh Abedinifar, Mohammad Mahdavi, Elham b. Rezaei, Mehdi Asadi and Bagher Larijani''Chan-Evans-Lam'' (CEL) reaction is the copper-mediated cross-coupling of N-nucleophiles with boronic acids that was independently reported in 1998 by Chan, Evans, and Lam for the first time. This reaction is accomplished at room temperature with a remarkably wide range of nucleophiles. In the recent decade, it has been particularly attractive as a convenient method for constructing the various C– N bonds in organic synthesis. Therefore, a comprehensive survey through all reported process was crucial. In this review, we summarized research progress about N-Arylation, based on the type of N-nucleophile involved in this reaction and catalysts from 2012 onwards.
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Barbiturates: A Review of Synthesis and Antimicrobial Research Progress
Authors: Madhvi, Divya Utreja and Shivali SharmaBackground: Barbituric acid and its derivatives have gained significant attention for several years as an indispensable class of compounds in the pharmaceutical industry due to their various biological activities, such as anticonvulsants, hypnotics, anti-diabetic, antiviral, anti-AIDS, anti-cancer, anti-microbial, and antioxidant, etc. A plethora of studies has shed light on the properties, synthesis, and reactivity of these compounds. The depiction of multiple biological activities by barbiturates compelled us, and by virtue of which herein we have mediated over the progress of synthesis of numerous kinds of compounds derived from barbituric acid with well-known and typical examples from 2016 to the present. Objectives: This review focuses on the advancements in methods of synthesis of barbituric acid derivatives and their applications as antimicrobial agents. Conclusion: This review will help future researchers to analyze the previous studies and explore new compounds for the development of efficient antimicrobial drugs.
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Comprehensive Account on the Synthesis of (-)-Balanol and its Analogues
Authors: Sajjad Ahmad, Rabia Akhtar and Ameer F. ZahoorBackground: A variety of diseases have been associated with hyperactivation of protein kinase C (PKC) enzymes such as cancer, diabetes, asthma, cardiovascular and central nervous system disorders. There is a dire need to selectively inhibit these enzymes by synthesizing new potent inhibitors. Balanol, a fungal metabolite belonging to the PKC inhibitor family, is especially included in this aspect. Tremendous effort has been put towards the synthesis of balanol by different research groups. Objectives: The aim of this review is to provide a detailed description of synthetic approaches adopted for the synthesis of key fragments of balanol (azepane and benzophenone). All the factors that resulted in excellent yield and high enantioselectivity have also been mentioned. Conclusion: It has been shown throughout this review that the synthesis of hexahydroazepine and benzophenone cores of balanol was achieved by employing a variety of important key steps with commercially available starting precursors, which make this total synthesis more valuable. Moreover, this article provides ideas to the synthetic as well as pharmaceutical chemists for the synthesis of (-)-balanol and its analogues.
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Recent Advancement in the One-pot Synthesis of the Tri-substituted Methanes (TRSMs) and their Biological Applications
Authors: Monika Verma, Ajay Thakur, Renu Sharma and Ruchi BhartiThe history of tri-substituted methanes (TRSMs) in chemical industries is much older. Tri-substituted methanes were previously used as dyes in the chemical industries. Still, there is a significant surge in researchers' interest in them due to their wide range of bioactivities. Trisubstituted methane derivatives show a wide range of biological activities like anti-tumor, antimicrobial, antibiofilm, antioxidant, anti-inflammatory, anti-arthritic activities. Due to the wide range of medicinal applications shown by tri-substituted methanes, most of the methodologies reported in the literature for the synthesis of TRSMs are focused on the one-pot method. This review explored the recently reported one-pot processes for synthesizing trisubstituted methanes and their various medicinal applications. Based on the substitution attached to the -CH carbon, this review categorizes them into two major classes: (I) symmetrical and (II) unsymmetrical trisubstituted methanes. In addition, this review gives an insight into the growing opportunities for the construction of trisubstituted scaffolds via one-pot methodologies. To the best of our knowledge, no one has yet reported a review on the one-pot synthesis of TRSMs. Therefore, here we present a brief literature review of the synthesis of both symmetrical and unsymmetrical TRSMs covering various one-pot methodologies along with their medicinal applications.
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High-component Reactions (HCRs): An Overview of MCRs Containing Seven or More Components as Versatile Tools in Organic Synthesis
Authors: Kobra Nikoofar and Fatemeh M. YielzolehAbstract: Recently, multi-component reactions (MCRs) have gained special attention due to their versatility for the synthesis of polycyclic heterocycles. Moreover, their applicability can become more widespread as they can be combined together as a union of MCRs. In this overview, the authors have tried to collect the MCRs containing more than seven components that can lead to effectual heterocycles in organic and/or pharmaceutical chemistry. The review contains papers published up to the end of 2020. The subject is classified based on the number of substrates, such as seven-, eight-, nine-, ten-, and more components. The authors expect their report to be helpful for researchers to clarify their route to significant MCRs.
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Asymmetric Organocatalytic Syntheses of Bioactive Compounds
Authors: Estibaliz Sansinenea and Aurelio OrtizBackground: The total syntheses of complex natural products have evolved to include new methodologies to save time, simplifying the form to achieve these natural compounds. Objectives: In this review, we have described the asymmetric synthesis of different natural products and biologically active compounds of the last ten years until the current day. Results: An asymmetric organocatalytic reaction is a key to generate stereoselectively the main structure with the required stereochemistry. Conclusion: Even more remarkable, the organocatalytic cascade reactions, which are carried out with high stereoselectivity, as well as a possible approximation of the organocatalysts activation with substrates are also described.
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Synthesis, Application and Antimicrobial Activity of New Acid Dyes Based on 3-Amino-2-thioxo-4-thiazolidinone Nucleus on Wool and Silk Fabrics
Authors: Fatma A. Mohamed, Shaban Elkhabiry, Ismail A. Ismail and Attia O. AttiaAbstract: The dyes are synthesized by 3-Amino-2-thioxo-4thiazolidinone (N-Amino rhodanine) with glutaraldehyde or terephthalaldehyde by 2:1 mole to form a and b then coupled with diazonium salts p- Amino benzenesulfonic acid and 4-Amino 3,4-disulfoazobenzeneazobenzene by 2:1 to form new different bis-mono-azo a1 and b1 and diazo a2 and b2 acid dyes. Therefore, the synthesized dyes were applied to both silk and wool fabric materials. We also evaluated the antimicrobial susceptivity of these dyed fabrics to two model gram-negative and gram-positive bacteria. Further, the chemical composition of these dyes is emphasized by an elemental analysis. Aims: This paper aims to synthesize and apply dye and antimicrobial to four new acid dyes based on derivatives of N-Amino rhodanine as a chromophoric group. Then, these dyes are used in dyeing silk and wool which have good lightfastness, and are also excellent for washing, rubbing and sweating fastness. Also, we measure antimicrobial susceptivity of silk and wool fabrics to Gram-negative and Gram-positive bacteria. Background: The new synthetic acid dyes, which have antimicrobial susceptivity to gram-negative and gram-positive bacteria, are mostly used on silk and wool fabrics which are excellent for lightfastness, washing, rubbing and sweating fastness. Objectives: The present studies aimed at synthesis, characterization and antimicrobial susceptivity to gramnegative and gram-positive bacteria. Methods: The infra-red spectrum was recorded using an Infra-red spectrometer, Perkin Elmer/1650 FTIR. The 1H-NMR spectra were recorded using a Varian 400MHz spectrometer. The absorbance of the dyes was measured in the ultraviolet-visible region between 300 and 700 nm by a UNICAM UV spectrophotometer. The dye uptake by wool and silk fabrics was measured using a Shimadzu UV-2401PC (UV/V is spectrophotometer at λmax) before and after dyeing. The produced dyes were found to have a good antimicrobial susceptivity to a variety of bacteria. Results and Discussion: The compounds a1, b1, a2 show good antimicrobial activity toward gramnegative (E. coli), gram-positive (S. aurous) bacteria. The data showed that exhaustion and fastness activities of silk and wool dyed fabrics were both very high. Conclusion: In this work, we prepared newly synthesized acid dyes based on 3-Amino-2-thioxo-4- thiazolidinone derivatives and used them for dyeing wool and silk fabrics. Both synthetic dyes have shown good lightfastness and fastness properties. Also, all dyes have shown a good antimicrobial effect.
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Efficient Synthetic Access to Novel Indolo[2,3-b]Quinoxaline-based Heterocycles
Authors: Ahmed Abdou O. Abeed, Talaat El-Emary and Sarah AlharthiBackground: This paper showed the synthetic capability of the indolo[2,3-b]quinoxaline nucleus to be provided as an excellent precursor for the synthesis of various heterocyclic compounds. These synthetic routes proceed via the formation of 3-(6H-indolo[2,3-b]quinoxalin-6-yl) propane hydrazide (2). The carbohydrazide 2 and its reactions with different reagents give five and six-membered rings, such as 1,3,4-thiadiazole, 1,3,4- oxadiazole, 1,2,4-triazole, and 1,2,4-triazine. Methods: All chemicals used in the current study were of analytical grade. Melting points were determined using an APP Digital ST 15 melting point apparatus and were uncorrected. FT-IR spectra were recorded on a Pye- Unicam SP3-100 and Shimadzu-408 spectrophotometers in KBr pellets and given in (cm-1) KBr. The NMR spectra were detected by a Bruker AV-400 spectrometer (400 MHz for 1H, 100 MHz for 13C and 40.55 MHz for 15N), Institute of Organic Chemistry, Karlsruhe, Germany. Chemical shifts were expressed as δ (ppm) with TMS as an internal reference. Mass spectrometry was provided on a Varian MAT 312 instrument in EI mode (70 eV). Results: The target compounds were obtained, and their structures were completely elucidated by various spectral and elemental analyses (Ft-IR, 1H-NMR, 13C-NMR, and mass spectrometry). Conclusion: The current work showed a view of the reactivity of the carbohydrazide group. The carbohydrazide 2 was obtained from the hydrazinolysis of carboethoxy compound 1 and exploited as a key intermediate to synthesize heterocyclic compounds with different rings.
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Volumes & issues
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Volume 21 (2024)
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Volume 20 (2023)
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Volume 19 (2022)
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Volume 18 (2021)
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Volume 17 (2020)
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Volume 16 (2019)
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Volume 15 (2018)
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Volume 14 (2017)
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Volume 13 (2016)
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Volume 12 (2015)
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Volume 11 (2014)
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Volume 10 (2013)
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Volume 9 (2012)
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Volume 8 (2011)
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Volume 7 (2010)
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Volume 6 (2009)
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Volume 5 (2008)
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Volume 4 (2007)
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Volume 3 (2006)
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Volume 2 (2005)
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Volume 1 (2004)