5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole
, Neni Frimayanti 2, Yuana Nurulita 1, Adel Zamri 1, Ihsan Ikhtiarudin 2 and Guntur Guntur 1,*
Round 1
Reviewer 1 Report
Authors reported the synthesis and fully characterization of 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole and its molecular docking study. I consider that manuscript could be accepted after minor revisions. Additional comments and suggestions are included:
(1) See title. Please, the first letter “F” in capital letter.
(2) See abstract, line 13. including instead of include.
(3) See Figure 1. The reaction conditions should be included on the arrow of each step like (i step) NaOH 12% (p/v), EtOH, 2 min, MW, and (ii step) AcOH, 85 °C, 24 h.
(4) See Figure 1. The yield of compounds 4 and 5 should be included. I consider that picture of the microwave equipment is not relevant; thus, it should be removed.
(5) See 2.1. Synthesis, lines 46-52. It is important to include in the discussion the yield of compounds 4 and 5.
(6) See 2.1. Synthesis, line 75. 1H and 13C NMR instead of 1H and 13C NMR.
(7) See 3.2. Synthesis of compound 4, line 117. (a) The IUPAC nomenclature for compound 4 could be included and (b) although compound 4 has been previously reported, I consider that yield, color of solid, and melting point should be included.
(8) See 3.3. Synthesis of compound 5, lines 125-143. (a) Synthesis of 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole 5 instead of synthesis of compound 5, (b) J = 5.8, J = 2.8 Hz instead of J = 5.8 dan J = 2.8 Hz, (c) J = 7.0 Hz instead of J = 7 Hz, and (d) infrared data should be added according to the discussion section.
(9) See 3.3. Synthesis of compound 5, lines 125-143. ¿Did you take 19F{1H}{13C} NMR spectra using CF3COOH as internal reference? It would be nice to include 19F NMR data and 19F NMR spectrum in the Manuscript and Supplementary Material, respectively. This information is optional by authors.
(10) See conclusion section. Authors mention that “Based on the molecular docking study, the compound 5 showed the potential inhibition against ERα”. I consider that additional relevant information could be included.
(11) See Supplementary Material. (a) For Figure S1 chemical shifts and integrations of all signals should be included, (b) for Figure S2 integrations of all signals should be included, and (c) for Figure S3 chemical shifts of all signals should be included.
(12) See Supplementary Material. The infrared spectrum of compound 5 should be included according to the discussion section.
Author Response
Please see the attachment, thank you.
Author Response File: 
Author Response.pdf
Reviewer 2 Report
The manuscript submitted by Guntur and co-workers describes the synthesis of a new fluorinated pyrazole, therefore the manuscript fits in Molbank guidelines. There are some concerns about the experimental part. The authors stated that the reaction was performed in acetic acid refluxing at 85°C. However, the boiling point of acetic acid is 118°C, so technically the reaction is heated at 85°C, but not refluxed. At line 49, NaOH seems used in excess and not in catalytic amount. I suggest also to revise the text since I have noticed several mistakes and typos. At page 3 of s.i. erase CDCl3 from the second spectra at the wrong chemical shift.
Author Response
Please see the attachment, thank you.
Author Response File: Author Response.pdf
Reviewer 3 Report
Dear authors,
the manuscript is a very interesting note concerning the synthesis and molecular docking studies of the new fluorinated pyrazole. The experimental part as well as the docking studies were well designed and performed.
I suggest you to revise the English version of the manuscript.
Author Response
Please see the attachment, thank you.
Author Response File: Author Response.pdf
