Inventing of Macrocyclic Formazan Compounds with Their Evaluation in Nano-Behavior in the Scanning Microscope and Chromatography

Abstract

Cyclic Formazan was invented and prepared for the first time by researcher Dr. Nagham Aljamali was established in April 2021. Therefore, it is considered one of the developed and modern compounds, which is described by a lack of references and researches. Therefore, the researcher, Dr. Nagham prepared and created a series of these compounds and studied several applications, including biological, pharmaceutical studies , also as antifungal, antibacterial, and anticancer agents, and here in this research, cyclic formazan was studied as medical nanomaterials. A number of technical spectroscopic studies have been used to demonstrate their chemical structures which provided clear evidences of their chemical structures via many technical instruments like (FT IR-Spectra , 1H.NMR-Spectra, Mass-Spectra)., Melting points, other studies represented by evolution them as Nano-compounds by {Scanning Electron Microscopy (FESEM) , and their Chromatographic behavior}.

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Copyright@ Nagham Mahmood Aljamali | Biomed J Sci & Tech Res | BJSTR. MS.ID.006616. 32783
Research Article
ISSN: 2574 -1241 DOI: 10.26717/BJSTR.2022.41.006616
Inventing of Macrocyclic Formazan Compounds with
Their Evaluation in Nano- Behavior in the Scanning
Microscope and Chromatography
Nagham Mahmood Aljamali*
Organic Chemistry, Synthetic Chemistry Field, Iraq
*Corresponding author: Nagham Mahmood Aljamali, Organic Chemistry, Synthetic Chemistry Field, Iraq
ARTICLE INFO ABSTRACT
Received: January 21, 2022
Published: February 01, 2022
Citation: Nagham Mahmood Aljamali.
Inventing of Macrocyclic Formazan Com-
pounds with Their Evaluation in Nano-
Behavior in the Scanning Microscope and
Chromatography. Biomed J Sci & Tech Res
41(3)-2022. BJSTR. MS.ID.006616.
          
Nagham Aljamali was established in April 2021. Therefore, it is considered one of the
developed and modern compounds, which is described by a lack of references and
researches. Therefore, the researcher, Dr. Nagham prepared and created a series of
these compounds and studied several applications, including biological, pharmaceutical
studies, also as antifungal, antibacterial, and anticancer agents, and here in this
research, cyclic formazan was studied as medical nanomaterials. A number of technical
spectroscopic studies have been used to demonstrate their chemical structures which
provided clear evidences of their chemical structures via many technical instruments
like (FT IR-Spectra , 1H.NMR-Spectra, Mass-Spectra)., Melting points, other studies
represented by evolution them as Nano-compounds by {Scanning Electron Microscopy
(FESEM), and their Chromatographic behavior}.
Keywords: Cyclic Formazan; Formazan; Imine; Schiff Base; Azo; Aldamine; Anil;
Scanning Electron Microscopy (FESEM); Chromatography
Introduction
Cyclo- Formazan is one of the modern compounds in the
   
    
time globally [1,2]. And because their studies and references are
a few for this cause the researcher Dr. Nagham Aljamali prepared
and carried out various compounds from Macrocyclic-Formazan
by using various conditions and different basic medium [3-7] like
(Pyridine ,Pipridine ,5 % Sodium hydroxide, Triethyl amine,…)
[3], and linked them with heterocyclic compounds and other
compounds with more than two hetero atoms to increase their
effectiveness [7-11] , biological [13,16] and industrial applications
[17,20]. Cyclic Formazan has cyclic structure of (-N=N=C-N- in
cyclic structure) or (-N=N-C-N-NH- in cyclic structure) according
to type of amine in reaction [1,2]., They were considered among
the organic compounds of importance in organic chemistry

chemistry [1,21-24], especially in coordination chemistry [25-27],
as a ligands because they contain free electrons of donor atoms
to coordinate with ions to form complexes [28-30]. Formazan also
tested in many studies as anti-bacterial [31-34] and anti-fungal
compounds [35-36] and types of cancer [37-39], especially breast
[40] and laryngeal cancers [41], as anti-bacterial [42] and anti-
fungal [43,44], and other studies [40-44].
Instruments and Experimental Part
        

Copyright@ Nagham Mahmood Aljamali | Biomed J Sci & Tech Res | BJSTR. MS.ID.006616.
Volume 41- Issue 3 DOI: 10.26717/BJSTR.2022.41.006616
32784
electro-thermal apparatus (Switzerland) in an open capillary
tube. FT.IR spectra were detailed on Fourier transform infrared
spectrometer (FT-IR) in (FT-IR- 3600) infrared spectrometer via
employing KBr Pellet technique., 1H.NMR spectra were recorded in
DMSO-d6 as solvent using (TMS) as internal standard and chemical
shifts are expressed as (δ ppm)., also Mass– Spectra for some
of them other studies represented by evolution them as Nano-
compounds by {Scanning Electron Microscopy (FESEM), and their
Chromatographic behavior}.
Procedures
Preparation of Compounds {1, 2, 3}: Terephthalic acid (0.01
mole) was dissolved in (30 ml) absolute ethanol (2ml) of Sulfuric
 
    
hrs) in presence of phosphoric acid as closing agent in cyclization
        
recrystallized to yield Ox diazole amine Compound [1], which

 
recrystallized to yield Oxadiazole hydrazine Compound [2], which
   
(3 hrs) in presence of (3 drops of glacial acetic acid), according to
   
Imine -Compound [3] (Scheme 1).
Scheme 1: Synthesis of Compounds {1, 2, 3}.
Creation of Inventive Macrocyclic Formazan Compound {4}:
Compound [3] was (0.01 mole) reacted in presence of (Pyridine)
with (0.01 mole) of diazo salt of p- phenyl diamine via many steps
in basic medium to formation Invented Macrocyclic Formazan
         
water, recrystallized to yield Invented Macrocyclic Formazan [4] by
following literatures [1,2].
Creation of Inventive Macrocyclic Formazan Compound {5}:
       
benzoic acid in presence of (2-3 drops) of glacial acetic acid for (2
hrs) in absolute ethanol according to procedure [4-7], the product
 
mole) was reacted in presence [1-3] of (Triethyl amine) with (0.01
mole) of diazo salt of p- phenyl diamine via many steps in basic
medium to formation Invented Macrocyclic Formazan after (12 hrs),

to yield Invented Macrocyclic Formazan [5] by following literatures
[1,2] (Scheme 2).

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Volume 41- Issue 3 DOI: 10.26717/BJSTR.2022.41.006616
32785
Scheme 2: Creation of Invented Macrocyclic Formazan Compounds {4, 5}.
Creation of Inventive Macrocyclic Formazan Compound{6}:
       
phenol in presence of (2-3 drops) of glacial acetic acid for (3 hrs) in

,dried ,recrystallized to yield Imine -Compound that (0.01 mole)
was reacted in presence [1,2] of (Pipyridine) with (0.01 mole) of
diazo salt of p- phenyl diamine via many steps in basic medium
to formation Invented Macrocyclic Formazan after (10 hrs), the
 
yield Invented Macrocyclic Formazan [6] by following literatures
[1,2].
Creation of Inventive Macrocyclic Formazan Compound{7}:
          
dimethylamine benzaldehyde in presence of (2-3 drops) of
glacial acetic acid for (2 hrs) in absolute ethanol according to
      
Imine -Compound that (0.01 mole) was reacted in presence [1-3]
of (5 % NaOH) with (0.01 mole) of diazo salt of p- phenyl diamine
via many steps in basic medium to formation Invented Macrocyclic
        
by distilled water, recrystallized to yield Invented Macrocyclic
Formazan [7] by following literatures [1,2] (Scheme 3).

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Volume 41- Issue 3 DOI: 10.26717/BJSTR.2022.41.006616
32786
Scheme 3: Creation of Invented Macrocyclic Formazan Compounds {6, 7}.
Results and Discussion
        
Formazan Compounds have been created in same procedure that
followed and invented [1,2] by Dr. Nagham in April 2021 that
got a patent to invention of Macrocyclic Formazan compounds,
then several studies were carried out to improve these innovative
         
spectra, FT.IR- Spectra, Mass- Spectra., other studies represented
by (Melting points, other studies represented by evolution them
as Nano-compounds via {Scanning Electron Microscopy (FESEM)
,and their Chromatographic behavior}., all the results are shown in

Spectral Investigation
FT.IR- Spectral Indication of Invented Macrocyclic
Formazan Compounds     
compounds by shifting of frequencies of Imine group (CH=N) in
starting compounds (Imine compounds) that were about at (1615
, 1610, 1618, 1620) Cm-1 respectively in all starting materials
of imine compounds that were shifted to (1630 , 1627 , 1631,
1642) Cm-1 for (-C=N-) due to formation of Macrocyclic Formazan,
also appearance of three bands due to partitions of azo group
of Formazan in Macrocycle (-N=N-) are (1429 ,1451, 1476) Cm-1
for (-N=N-C-) in compound {4}., and other compound like this., all

1H.NMR- Spectral Indication of Invented Macrocyclic
Formazan Compounds: The second characterization of innovative
compounds by disappearance of peak for imine group (CH=N) in
starting compound (Imine compound) that were at δ (8.13) in
Compound {3} (starting compound) due to formation of (N=C-
N=N) for (Formazan groups) in innovated compounds [4, 5, 6, 7],
also in compound [5] appeared peak at δ (12.31) due to proton of
carboxyl group (COOH), while compound [6] appeared peak at δ
(10. 82) due to proton of hydroxyl group (OH), all peaks explained
according to reference [33].
Mass– Spectral Indication of Invented Macrocyclic
Formazan Compounds: The third characterization of inventive
compounds by partition of innovative cyclic compounds via
appearance of fragments in spectra in (Figures 1 & 2).
Other Characterization: All Invented Macrocyclic Formazan
derivatives were studied to collect all the chemical and physical
properties, in (Table 1).

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Figure 1: Mass–Spectrum of Invented Macrocyclic Formazan Compound [4].
Figure 2: Mass–Spectrum of Invented Macrocyclic Formazan Compound [7].
Figure 3: Scanning Electron Microscopy of Invented Cyclic Formazan [4].

Copyright@ Nagham Mahmood Aljamali | Biomed J Sci & Tech Res | BJSTR. MS.ID.006616.
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Table 1: Other characterization of Invented Macrocyclic Formazan Compounds.
Innovated Comps. P % Color M .P C° Rf Solvents (TLC)
Innovated Comp.{1} 76 Bill Yellow 160 0.62 Ethanol : Dioxan
Innovated Comp.{2} 76 Deep Yellow 184 0.56 Ethanol : Dioxan
Innovated Comp.{3} 74 Yellowish Orange 198 0.6 Ethanol : Dioxan
Innovated Comp.{4} 86 Reddish Yellow 214 0.66 Ethanol : Dioxan
Innovated Comp.{5} 82 Orange 226 0.58 Ethanol : Dioxan
Innovated Comp.{6} 86 Reddish Orange 220 0.6 Ethanol : Dioxan
Innovated Comp.{7} 80 Orange 228 0.62 Ethanol : Dioxan
Scanning Electron Microscopy (FESEM): Scanning Electron
Microscopy (FESEM) of the Innovated Cyclic Formazan compounds
(for morphological properties) that revealed in this research that
they have a spherical shape and have granular sizes within the
Nano-scale they have an average size of (44. 23 , 40. 12 , 46. 61,
55. 97) nanometers for Cyclic Formazan Compounds [4, 5, 6, 7]
respectively, so the surface area increases and this characteristic
makes it eligible for medical uses because it has a small granular
size , spherical shape within the nano-scale that is used in medical
            

Figure 4: Scanning Electron Microscopy of Invented Cyclic Formazan [5].
Figure 5: Scanning Electron Microscopy of Invented Cyclic Formazan [6].

Copyright@ Nagham Mahmood Aljamali | Biomed J Sci & Tech Res | BJSTR. MS.ID.006616.
Volume 41- Issue 3 DOI: 10.26717/BJSTR.2022.41.006616
32789
Figure 6: Scanning Electron Microscopy of Invented Cyclic Formazan [7].
Chromatographic Study for Invented Cyclic Formazan
Compounds: This section of the study involved a study of the
chromatographic separation of the invented cyclic formazan
compounds to know the effect of the effective groups in the chemical
composition on the separation according to procedures [39-43],
such as polar groups. In this work, Cyclic Formazan Compound
{5} is the slowest compound in the separation because it contains
two polar carboxyl groups (OH) that are affected when descending
during the season and followed by Cyclic Formazan compound {6}
according to polarity, then compound [4], and last one is compound
[7], for this reason the compound [7] separated faster than other
compounds due to its structure is less polarity and less interaction
with column, (Figures 7-10).
Figure 7: Chromatogram of Invented Cyclic Formazan Compound [4].
Figure 8: Chromatogram of Invented Cyclic Formazan Compound [5].

Copyright@ Nagham Mahmood Aljamali | Biomed J Sci & Tech Res | BJSTR. MS.ID.006616.
Volume 41- Issue 3 DOI: 10.26717/BJSTR.2022.41.006616
32790
Figure 9: Chromatogram of Invented Cyclic Formazan Compound [6].
Figure 10: Chromatogram of Invented Cyclic Formazan Compounds [7].
Conclusion
All Invented Macrocyclic Formazan compounds gave good
evidences for their structures via various spectral techniques, also
some of them studied like scanning microscope appeared Nano-
properties for these compounds, which means that the cyclic
Formazan compounds can be good drug delivery to treatment and
medical applications.
Conict of Interest

Funding Source
None.

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Volume 41- Issue 3 DOI: 10.26717/BJSTR.2022.41.006616
32791
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Products. 2021; (1st Edn.)., Eliva Press SRL.
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Synthetic Chemistry. Evince pub Publishing house.
8. Nagham Mahmood Aljamali, Imd Kam (2020) Development of
Trimethoprim Drug and Innovation of Sulfazane-Trimethoprim
Derivatives as Anticancer Agents. Biomedical & Pharmacology Journal
13(2): 613-625.
9. Imd Kam, Hasaneen Kudhair Abdullabass, Nagham Mahmood Aljamali

of Cancerous Tumors. Journal of Cardiovascular Disease Research, p. 44-
55.
10. Nagham Mahmood Aljamali (2018) Reactions and Mechanisms. IJMRA
Publication.
11. Matheus ME, de Almeida Violante F, Garden SJ (2007) Isatins inhibit
cyclooxygenase-2 and inducible nitric oxide synthase in a mouse
macrophage cell line. Eur J Pharmacol 556: 200-206.
12. Nagham Mahmood Aljamali (2016) Synthesis and Biological Study of
Hetero (Atoms and Cycles) Compounds. Der Pharma Chemica, p. 40-48.
13. Nagham Mahmood Aljamali (2015) Synthesis and Chemical

J Pharm and Tech 8(1): 78-84.
14. Mestaf M, Nawfel Muhammed Baqer Muhsin (2019) Neuro Quantology.
17(11): 11-16.
15. Nagham Mahmood Aljamali (2015) Review in Azo Compounds and its
Biological Activity. Biochem Anal Biochem 4: 169.
16. Nagham Mahmood Aljamali, SF Jawad, (2022) Preparation, Spectral
Characterization, Thermal Study, and Antifungal Assay of (Formazane
-Mefenamic acid) - Derivatives. Egypt J Chem 411 65(2).
17. Nagham Mahmood Aljamali (2017) Synthesis of Antifungal Chemical
Compounds from Fluconazole with (Pharma-Chemical) Studying.
Research journal of Pharmaceutical, biological and chemical sciences
8(3): 564 -573.
18. MN Abdmajed, Nagham Mahmood Aljamali (2021) Preparation of
Benzothiazole-Formazane Reagents and Studying of (Spectral, Thermal,
Scanning Microscopy, Biological Evaluation). International Journal of
Pharmaceutical Research 13(1): 4290-4300.
19. Mad M, Nagham Mahmood Aljamali, Nadheema AA (2018) Preparation,
Spectral Investigation, Thermal Analysis, Biochemical Studying of New
(Oxadiazole -Five Membered Ring)-Ligands. Journal of Global Pharmacy
Technology 10(1): 20-29.
20. Nagham Mahmood Aljamali (2020) Survey on Methods of Preparation
and Cyclization of Heterocycles. International Journal of Chemical and
Molecular Engineering 6(2): 19-36.
21. Mid M, Nagham Mahmood Aljamali, Wassan Ala Shubber, Sabreen Ali
Abdalrahman (2018) New Azomethine- Azo Heterocyclic Ligands Via
Cyclization of Ester. Research Journal of Pharmacy and Technology
11(6): 2555-2560.
22. Hasaneen Kudhair Abdullabass, Aseel Mahmood Jawad, Nagham
Mahmood Aljamali (2020) Synthesis of drugs derivatives as inhibitors of
cancerous cells. Biochem Cell Arch 20(2): 5315-5322.
23. Aseel Mahmood Jawad, Nagham Mahmood Aljamali (2020) Innovation,
Preparation of Cephalexin Drug Derivatives and Studying of (Toxicity
& Resistance of Infection). International Journal of Psychosocial
Rehabilitation 24(04): 3754-3767.
24. Husen Ali Ahmd, Nagham Mahmood Aljamali (2021) Preparation,
Characterization, Antibacterial Study, Toxicity Study of New Phenylene
diamine- Formazan Derivatives. Indian Journal of Forensic Medicine &
Toxicology 15(2): 3102-3112.
25. Nagham Mahmood Aljamali, Hussein Mejbel Azeez (2021) Synthesis and

Breast Cancer Cells. Annals of RSCB 25(3): 8562-8578.
26. Nagham Mahmood Aljamali, Asmaa Kefah Mahdi (2021) Synthesis,

via Thiosemicarbazide. Annals of RSCB 25(3): 8521-8537.
27. F Jawad, Nagham Mahmood Aljamali (2021) Preparation, Investigation
and Study of Biological Applications of Tyrosine Derivatives against
Breast Cancer Cells. NeuroQuantology 19(9): 117-125.
28. Nagham Mahmood Aljamali, Intisar Obaid Alfatlawi (2015) Synthesis
of Sulfur Heterocyclic Compounds and Study of Expected Biological
Activity. Research J Pharm and Tech 8(9): 1225-1242.
29. Intisar Obaid Alfatlawi, Nuha SS, Zainab MJ, Nagham Mahmood Aljamali
(2017) Synthesis of New Organic Compounds Via Three Components

on Bacteria of Teeth). Journal of Global Pharma Technology 11(9): 157-
164.
30. Nagham Mahmood Aljamali, Saher Mahmood Jawd, Zainab MJ, Intisar
Obaid Alfatlawi (2017) Inhibition activity of (Azo–acetyl acetone) on
bacteria of mouth. Research Journal of Pharmacy and Technology 10(6):
1683-1686.
31. Aseel Mahmood Jawad, Nagham Mahmood Aljamali, Saher Mahmood
       
Derivatives for Treatment of Microbial Contamination in Hospitals and
Environment. Indian Journal of Forensic Medicine & Toxicology 14(2):
1115-1122.
32. Nagham Mahmood Aljamali (2022) Spectral and Laboratory Diagnostics
of Compounds. (1st Edn.)., Eliva Press SRL.
33. Shireen R Rasool, Nagham Mahmood Aljamali, Ali Jassim Al-Zuhairi
(2020) Guanine substituted heterocyclic derivatives as bioactive
compounds. Biochem Cell Arch 20(2): 3651-3655.
34. Deniz Ar, Alexander FR Kilpatrick, Beatrice Cula, Christian Herwig,
Christian Limberg (2021) Transformation of Formazan ate at Nickel(II)
Centers to Give a Singly Reduced Nickel Complex with Azoiminate

Copyright@ Nagham Mahmood Aljamali | Biomed J Sci & Tech Res | BJSTR. MS.ID.006616.
Volume 41- Issue 3 DOI: 10.26717/BJSTR.2022.41.006616
32792
Radical Ligands and Its Reactivity toward Dioxygen. Inorganic Chemistry
60(18): 13844-13853.
35. Francesca Milocco, Folkert de Vries, Harmke S Siebe, Silène Engbers,
Serhiy Demeshko, et al. (2021) Widening the Window of Spin-Crossover
Temperatures in Bis(formazanate)iron(II) Complexes via Steric and
Noncovalent Interactions. Inorganic Chemistry 60(3): 2045-2055.
36. Abd Ali H, Nagham Mahmood Aljamali (2021) Chalcone-Heterocyclic
     
International Journal of Pharmaceutical Research 13(1): 4234-4242.
37. Nor A, Sud S, Nagham Mahmood Aljamali (2019) Synthesis,
Characterization and Thermal Analysis for New Amoxil Ligands. Asian
Journal of Chemistry 31(5): 1022-1026.
38.          
(2020) Synthesis of Triazole Derivatives via Multi Components Reaction
and Studying of (Organic Characterization, Chromatographic Behavior,
Chem-Physical Properties). Egypt J Chem 63(11): 4163-4174.
39. Nagham Mahmood Aljamali (2018) Synthesis, Investigation,
Chromatography, Thermal) - Behavior of (Five, Seven) - Membered Ring
with Azo and Anil Compounds. Pak J Biotechnol 15(1): 219-239.
40. Mhammd Abdul, Abd Ali H, Nagham Mahmood Aljamali (2021)
Synthesis, Spectral, Bio Assay, Chromatographic - Studying of New
Imidazole Reagents Via Three Components Reaction. NeuroQuantology
19(7): 115-122.
41. Nagham Mahmood Aljamali (2019) Separations of Samples Contents
(Vitality, Environmental, Chemical) By Instrumental & Laboratory
Methods. 1 (Eds.)., Evince pub Publishing.
42. Nagham Mahmood Aljamali, Tabark Emad Al-Faham (2021)
      
Phenylenediamine Derivatives. Annals of RSCB 25(4).
43. Nagham Mahmood Aljamali, Jad F (2021) Preparation, Diagnosis and
Evaluation of Cyclic-Tryptophan Derivatives as Anti Breast Cancer
Agents. Biomed Pharmacol J 14(4).
44. Mid Mohmd, Nagham Mahmood Aljamali, Sabreen Ali Abdalrahman,
Wassan Ala Shubber (2018) Formation of Oxadiazole Derivatives
Ligands from Condensation and Imination Reaction with References To
Spectral Investigation, Thermal and Microbial Assay. Biochem Cell Arch
18(1): 847-853.
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DOI: 10.26717/BJSTR.2022.41.006616
Nagham Mahmood Aljamali. Biomed J Sci & Tech Res