(E)-1-(5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one Oxime
and Gamal A. El-Hiti 5,*
Round 1
Reviewer 1 Report
The Ms. “(E)-1-(5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl) ethan-1-2 one oxime” describes the reaction of 1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl) ethan-1-one with excess hydroxylamine hydrochloride (2 mole equivalents) in dry ethanol.
The work can be published in Molecules after the authors answer the following questions:
- The Introduction should be rewritten since in the present form it repeats known concepts
- In the section 2.1. Synthesis, the authors should provide more information
- Same for other sections
In my opinion the work describes a simple reaction, taking previous works as reference. As the authors themselves say in the Introduction “the current work involves the synthesis of a novel heterocycle containing both oxime and 1,2,3-triazole moieties” the most useful thing about Ms. is the synthesis of a new compound. For these reasons I consider that the work could be published once rewritten expanding some concepts
Author Response
Re: molbank-2193346 R1
Response to Reviewers
The authors appreciate the valuable comments made by the reviewers. Please find enclosed our response to their comments.
Reviewer 1
In my opinion the work describes a simple reaction, taking previous works as reference. As the authors themselves say in the Introduction “the current work involves the synthesis of a novel heterocycle containing both oxime and 1,2,3-triazole moieties” the most useful thing about Ms. is the synthesis of a new compound. For these reasons I consider that the work could be published once rewritten expanding some concepts. The work can be published in Molecules after the authors answer the following questions.
Thanks for the revisions and the comments which we have answered.
1) The Introduction should be rewritten since in the present form it repeats known concepts
The introduction section has been expanded and four new references have been cited.
2) In the section 2.1. Synthesis, the authors should provide more information
Section 2.1 was expanded a bit in which the following text was added. “The progress of the reaction was tested using thin layer chromatography. A reflux for 5 hours was need for the reaction to be completed”.
3) Same for other sections.
Section 2.2 was expanded a bit in which the following text was added. “The protons of the aryl ring appeared as two doublets (J = 9.1 Hz) at 7.92 and 8.4q ppm” and “While C1 and C4 of the aryl ring appeared at 145.8 and 152.9 ppm, respectively”.
Author Response File: 
Author Response.pdf
Reviewer 2 Report
Wahab and co-workers reported the synthesis of the oxime-based-1,2,3-triazole heterocyclic scaffold. The manuscript may be suitable for publication after addressing the comments below.
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1. |
First, the reaction conditions are commonly used for synthesizing imines, and I don't see any novelty in this work. Moreover, what is the author's aim in making this compound? If this is the purpose of medicinal chemistry, it would be good if the authors investigated the pharmacological activities. |
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2. |
Abstract: The authors stated “different techniques” please include what techniques have been established to identify the structure. |
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3. |
The authors should write the biological importance of privileged oxime-based-1,2,3-triazole heterocyclic motifs in drug discovery and cite the following article to expand references 22. EJMC 114 (2016) 293-307 (https://doi.org/10.1016/j.ejmech.2016.03.013) & EJMC 188 (2020) 111974 (https://doi.org/10.1016/j.ejmech.2019.111974). |
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4. |
What is the author's rationality behind this synthesis, especially -NO2 substituted products? If the authors make more SAR compounds, it will strengthen the manuscript. |
Author Response
Re: molbank-2193346 R1
Response to Reviewers
The authors appreciate the valuable comments made by the reviewers. Please find enclosed our response to their comments.
Reviewer 2
Wahab and co-workers reported the synthesis of the oxime-based-1,2,3-triazole heterocyclic scaffold. The manuscript may be suitable for publication after addressing the comments below.
Thanks for the revisions and the comments which we have answered.
1) First, the reaction conditions are commonly used for synthesizing imines, and I don't see any novelty in this work. Moreover, what is the author's aim in making this compound? If this is the purpose of medicinal chemistry, it would be good if the authors investigated the pharmacological activities.
The comment will be taken into consideration for related future work. To clarify the aim of the current research, the last paragraph of the introduction section has been modified to read as follows. “The aim of the current work was to synthesize a novel heterocycle containing both oxime and 1,2,3-triazole moieties. using a facile and routine method. The synthesis of such a compound opens gates for the production of a series of derivatives containing various substituents to test their effect on the biological activities of 1,2,3-triazoles containing oxime”.
2) Abstract: The authors stated “different techniques” please include what techniques have been established to identify the structure.
The term “different techniques” in the abstract has been replaced with “nuclear magnetic resonance spectroscopy and single crystal x-ray along with the elemental analysis”.
3) The authors should write the biological importance of privileged oxime-based-1,2,3-triazole heterocyclic motifs in drug discovery and cite the following article to expand references 22. EJMC 114 (2016) 293-307 (https://doi.org/10.1016/j.ejmech.2016.03.013) & EJMC 188 (2020) 111974 (https://doi.org/10.1016/j.ejmech.2019.111974).
The biological importance of privileged oxime-based-1,2,3-triazole heterocyclic motifs in drug discovery has been discussed and the two suggested references have been cited. The following text has been added to the introduction section. “For example, several novel 1,2,3-triazoles have been synthesized and their anticancer activity was investigated. Some of the synthesized 1,2,3-triazoles showed potential as anticancer (e.g., lung cancer) drugs [23,24]”.
- Chandrashekhar, M.; Nayak, V.L.; Ramakrishna, S.; Mallavadhani, U.V. ,Novel triazole hybrids of myrrhanone C, a natural polypodane triterpene: Synthesis, cytotoxic activity and cell based studies. Eur. J. Med. Chem. 2016, 114, 293–307. https://doi.org/10.1016/j.ejmech.2016.03.013.
- Madasu, C.; Karri, S.; Sangaraju, R.; Sistla, R.; Uppuluri, M.V. Synthesis and biological evaluation of some novel 1,2,3-triazole hybrids of myrrhanone B isolated from Commiphora mukul gum resin: Identification of potent antiproliferative leads active against prostate cancer cells (PC-3). Eur. J. Med. Chem. 2020, 188, 111974. https://doi.org/10.1016/j.ejmech.2019.111974.
4) What is the author's rationality behind this synthesis, especially -NO2 substituted products? If the authors make more SAR compounds, it will strengthen the manuscript.
The last paragraph of the introduction section has been modified to answer the comment. Currently, we are in the process of synthesizing a range of compounds in which the nitro group is replaced by many others to test the effect of substituents on the biological activities of the 1,2,3-triazole ring system.
Author Response File: Author Response.pdf
Round 2
Reviewer 1 Report
The authors have responded satisfactorily to all the referees’ request. Therefore the Ms. can be published in Molbank
