Synthesis, and Anticancer Evaluation of 4-[(Indol-3-yl)-arylmethyl]-1-phenyl-3-methyl-5-pyrazolone Derivatives via a Magnetic Aminated Starch Biocatalyst
, Mona Pourjafar 2 and Esmaeel Sharifi 3,4Round 1
Reviewer 1 Report
The manuscript by Ali et al can be accepted after addressing important concerns described in the next section.
Comments for author File: 
Comments.pdf
The manuscript by Ali et al can be accepted after addressing the following concerns.
1. Why the Figure legends are mentioned two times (above and below the figure)
2. Figure 7; pointing of the curved arrows is not correct and the structure of pyrazole is not correct.
3. There are several typos in the manuscript and sentences start with a number (see the attached file).
4. Authors should give citations of recent reviews of pyrazoles/pyrazolones to show the general importance of these compounds such as this review article.
https://www.future-science.com/doi/abs/10.4155/fmc-2021-0275
https://doi.org/10.4155/fmc-2021-0275
Author Response
Please see the attachment
Author Response File: Author Response.pdf
Reviewer 2 Report
In this interesting manuscript by Ramshini et al. a magnetically active composite was prepared and applied for the catalysis of selected three-component condensation reaction using indole, aromatic aldehydes and model pyrazolone derivative. The title biocatalyst was made of starch functionalized with primary amino groups (derived from p-phenylenediamine) by co-precipitation with the in situ generated Fe3O4. The resulting material could be reused to catalyze the model Michael-type addition for five consecutive cycles to give the expected product in comparable yield. The structure of the catalyst was analyzed by appropriate methods. In addition, anticancer activity of selected final products was briefly analyzed against MCF-7 lines to demonstrate noteworthy selectivity in comparison with normal cells (typically ca. two orders of magnitude). The paper can be of some interest to the readers, but it require corrections.
Major issues:
(a) First of all, the structure of starch (shown in Figs 1,2, and 6) is not correct (stereochemistry!). As it is made of glucose, the OH group at C(4) of the pyrane ring should be equatorial.
(b) the structure of composite in Fig.1 differs from that in Fig.2; in the former structure additional additional phenylenediamine group at C(3) of glucose ring is shown. Which one is correct? This should be discussed in detail in the main body.
(c) table 1 and the text: a reference experiment with no catalyst added should be supplemented and discussed.
(d) Fig.7: the black arrows used to indicate electron movements should be used precisely. It should start from the appropriate electron pair towards the electrophilic center. For example, in structure (I) the arrow starts at H atom of the NH2 group and leads to somewhere between C-C and the neighboring C-H bonds. This is clearly incorrect.
At the same scheme, the inner double bond in pyrazolone (keto tautomer shown at the right up corner) must be removed.
(e) the observed cytotoxicity should be compared with activity of reference drug (e.g. doxorubicin)
Further minor comments:
(d) reaction temperatures shown in Fig.2 are not consistent with those discussed in the main body and experimental part
(e) neither Fig.1, Fig.2 nor Fig.7 are actually figures; these are schemes.
(f) as to the wavenumbers discussed in line 148, p.5 there is ‘117’, should be ‘1177’.
(g) Table 2. The structure of product 6b is missing.
(h) some of the obtained products are characterized by high melting points (e.g. 6e, mp 239-241); no decomposition could be observed at such transition temp?
(i) references: ref[9] – no such reference could be found; ref[17] – editing required; ref[21] – title is missing
Also, the manuscript requires thorough language checking, for example: p.2. Line 51: there is ‘significant great’ phrase; p.2, lines 59/60: repetition ‘various’; p.2 lines 66/67: ‘considering these consideration’ etc.
Author Response
Please see the attachment
Author Response File: Author Response.pdf
Reviewer 3 Report
This research article by Seied Ali Pourmousavi and coworkers reported the synthesis of aminated starch biocatalyst and used it to prepare 4-[(Indol-3-yl)-Arylme-thyl]-1-Phenyl-3-Methyl-5-pyrazolone derivatives (more than 25 examples). Importantly, the author conducted the anticancer study to evaluate the anticancer abilities of these pyrazolone derivatives. The author provides enough research data and convincing conclusions. But the format and English of the manuscript need to further improve. The author should be very careful about the format, especially the references, all the reference format is chaos. In general, the manuscript deserves to be published in Catalysts after minor revision.
1) The English of the manuscript need urgently polish, there are many sentences have grammatical errors, the author can invite some native English speakers help polish. For example, line 50-52, “The magnetite…” sentence is difficult understand, (1) “significant great interest” should be “great interest” or “significant great interest”, (2) “The magnetite nanoparticles … shown … interest… among researchers” that’s not logical, should be “researchers… shown … interest…in magnetite nanoparticles”.
2) Line 21, “1HNMR” should be “1H NMR”, same correction to others.
3) When cited reference, the author should put the reference in suitable location, for example lines 85-86: “Nouri et al., recipe with minor modifications [27]” should be “Nouri et al.[27] with minor modifications”, because [27] is from Nouri et al. instead of modifications.
4) Line 103, what’s the “Fe(III) and Fe(II)”, FeCl3 and FeCl2 (?) in the synthesis method the author should provide as much detail as possible.
5) Page 8, the TsSt NMR is not clean, except H-7, H-8 there are another 3 peaks, what is that peak? Please indicate it in the NMR.
6) All compounds’ names should be bold, “(6j, 6l, 6p, 6r, and 6y)” should be “6j, 6l, 6p, 6r, and 6y”, same correction to all manuscript.
7) All reference format is chaos, please read author instruction carefully.
The English of the manuscript need urgently polish, there are many sentences have grammatical errors, the author can invite some native English speakers help polish. For example, line 50-52, “The magnetite…” sentence is difficult understand, (1) “significant great interest” should be “great interest” or “significant great interest”, (2) “The magnetite nanoparticles … shown … interest… among researchers” that’s not logical, should be “researchers… shown … interest…in magnetite nanoparticles”.
Author Response
Please see the attachment
Author Response File: Author Response.pdf
Round 2
Reviewer 1 Report
The authors have addressed my concerns. I recommend the publication of this manuscript.
The authors have addressed my concerns. I recommend the publication of this manuscript.
