A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity

doi:10.21203/rs.3.rs-510455/v1

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A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity

https://doi.org/10.21203/rs.3.rs-510455/v1

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published 22 Jul, 2021

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A new magnetic supported manganese-based coordination complex (Fe₃O₄@SiO₂@CPTMS@MBOL@ Mn) was prepared in consecutive stages, characterized via various techniques (VSM, SEM, TEM, XRD, FT-IR, EDX, TG-DTA and ICP) and used as a capable nano-catalyst for the fast and green synthesis of divers 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones in a simple and efficient procedure from the one pot three-component condensation reaction of aldehydes, dimedone and phthalhydrazide in refluxed ethanol in excellent yields and fast reaction times. The Mn catalyst can be recycled and reused without notable loss of the catalytic activity. Also, the antibacterial properties of the Mn supported nano-catalyst were studied against a number of gram-positive and gram-negative bacterial strains.

Medicinal Chemistry

Inorganic Chemistry

Organic Chemistry

Aldehyde

Dimedone

Indazolophthalazinetrione

Phthalhydrazide

The Mn supported nano-catalyst

Phthalazine derivatives have an important role in heterocyclic compounds that have received terrific interests in the field of pharmaceutical and biological activities that leads to clinical application¹ such as antifungal², anti-inflammatory,³ anticonvulsant,⁴ anticancer,⁵ cardiotonic. ⁶ In addition, these compounds represents specific optical properties. ⁷

Multi-component reactions (MCRs) are notable mechanism for preparation of wide variety of organic compounds via better efficiency in one step with at least three or more starting materials.⁸ Using a large number of different type of catalysts which accelerate or proceed the reaction in smooth condition have been extensively developed for these reactions.^9–11 Several synthetic routes have been reported for the synthesis of Phthalazine derivatives such as one-pot three- or four- component condensation reactions.^12–16 For example, Fe₃O₄@Cys–SO₃H was used by Kefayati and coworker as a catalyst for the one-pot three-component condensation of aromatic aldehydes, phthalhydrazide and 1,3-dicarbonyl compounds for the synthesis of 2H-indazolo[2,1-b]phthalazinetriones derivatives in ethanol at refluxed condition.¹⁷ Shirini and coworkers applied [PVPH]ClO₄ as an efficient and reusable solid acid polymeric catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine- triones in the same way of using initial regents through the one-pot reaction at 100°C in solvent-free conditions.¹⁸ Heirati and coworkers investigated implementation of O-sulfonic acid poly(4-vinylpyrrolidonium) chloride as an effective catalyst for the same synthesis at 80°C in solvent-free conditions.¹⁹ Rostamnia and co-worker synthesized a series of 1H-indazolo[1,2-b]phthalazine-1,6,11-triones by similar regents and using the Fe₃O₄@GO-Pr-SO₃H catalyst in refluxed ethanol.²⁰ 5-sulphosalicylic acid was used by Karhale and coworkers as an organocatalyst catalyst for the one-pot synthesis of 2H-indazolo[2,1-b]phthalazinetriones from the previous substrates.²¹ Varghese and coworkers through a noticeable method synthesized 2H-indazolo[2,1-b]phthalazine-1,6, 11(13H)-triones by similar regents in the presence of iodine under ultrasonic irradiation.²² Mosaddegh and coworkers succeeded to synthesize phthalazinetriones derivatives through a rapid, one-pot, four-component route by using Ce(SO₄)₂· 4H₂O at 125°C and under solvent free condition.²³ However, some methods suffer from some limitations such as tedious workup procedures, using corrosive catalysts, low product yields, long reaction times, formation of side products and difficulties in recovery of catalysts.²⁴

Due to concerns on environmental issues different strategies were applied to reduce side- effects of chemical industries, for instance using solvent-free techniques, eco-friendly materials, ultrasound or microwave methods and finally recyclable catalysts.²⁵ In recent years the application of magnetic nanoparticles (MNPs) according to the super magnetic property and facile separation from reactions media, high surface area, low toxicity, biocompatibility, good stability, low cost has obtained noticeable regards for chemists using as catalysts in chemical reactions. Moreover, MNPs can be functionalized completely via proper surface modifications. Based on mentioned properties, many MNPs-supported catalysts have been effectively applied for improving a large number of chemical reactions. ^{26, 27} Among the heterogeneous catalysts, the magnetic supported metal complexes have special places, ²⁸ so we would like to announce the synthesis a novel Mn supported nano-catalyst (Fe₃O₄@SiO₂@CPTMS@MBOL@Mn) in consecutive stages (Scheme 1).

Then, the Mn supported nano-catalyst was characterized by various techniques (VSM, SEM, TEM, XRD, FT-IR, EDX, TG-DTA and ICP) and used as a capable nano-catalyst for the synthesis of divers 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones in a simple and efficient procedure from the one pot three-component condensation reaction of aldehydes, dimedone and phthalhydrazide in refluxed ethanol in good yields and fast reaction times (Scheme 2).

2.1 Characterization of the Mn supported nano-catalyst

Structure of the Mn supported nano-catalyst was approved utilizing the FT-IR, ICP, VSM, XRD, EDX, TEM, SEM, and TG-DTA.

2.1.1 ICP analysis of the Mn supported nano-catalyst

The Mn content in Fe₃O₄@SiO₂@CPTMS@MBOL@Mn was achieved about 0.27% by The ICP analysis.

2.1.2 FT-IR spectroscopy of the Mn supported nano-catalyst

Figure 1 illustrates the FT-IR spectra for each step of preparation of nano catalyst that includes A) Fe₃O₄ MNPs, B) Fe₃O₄@SiO₂, C) Fe₃O₄@SiO₂@ CPTMS, D) Fe₃O₄@SiO₂@CPTMS@MBOL and E) Fe₃O₄@SiO₂@CPTMS@MBOL@Mn. In part A existence of stretching vibrations peak for Fe-O is characteristic at about 578 cm^− 1. Appearing of a wide peak close by 1087 cm^− 1 in part B indicates the coating of silica with magnetite nanoparticles. Part C exhibits a unique peak at about 583 cm^− 1 confirming the presence of the C-Cl bond. Part D shows two newly discovered peaks at 1345 and 1664 cm^− 1 which are corresponded to the C-N and C = N bonds, respectively. Part E indicates a shift from 1664 to 1602 cm^− 1 which could be in accordance of the new interaction of manganese with the nitrogen of the C = N bond. Also at 408.93 cm^− 1 a weak peak was appeared in corresponding to the Mn-N band. Therefore, comparison of the all IR spectra approved the successful formation of the Mn supported nano-catalyst.

2.1.3 XRD analysis of the Mn supported nano-catalyst

In order to evaluate the crystallographic structure of Fe₃O₄@SiO₂@CPTMS@MBOL@Mn, the XRD analysis was carried out for Fe₃O₄@SiO₂ (grey, A), Fe₃O₄@SiO₂@CPTMS (red, B), Fe₃O₄@SiO₂@CPTMS@MBOL (blue, C) and Fe₃O₄@SiO₂@CPTMS@MBOL@Mn (green, D) and shown in Fig. 2. The diffraction peaks at 2θ = at 10, 30, 35, 45, 53, 57 and 63 approve the silica coated on the cubic spinel crystal planes of Fe₃O₄ effectively. The XRD pattern of Fe₃O₄@SiO₂@CPTMS@MBOL@M indicates the crystalline nature of the nano catalyst at 2θ = 30, 35, 39, 43, 56 which responded to the Mn catalyst. Through Debye Scherrer formula the particle size was obtained about 34.68 nm. In fact, due to the reduction of intensity the core-shell structure could be anticipated and the Fe₃O₄ MNPs particles were coated with ligand profitably.^29–31

2.1.4 EDX analysis of the Mn supported nano-catalyst

The elemental structure of the Mn supported nano-catalyst was disclosed by the EDX analysis (Fig. 3). The results ratified the existence of the predictable elements in the construction of the catalyst, including C, N, O, Si, S, Fe and Mn. Generally the sample will be usually coated with a very thin layer of gold that leads appearing of the Au peak in the EDX graph analysis, as well.

2.1.5 SEM and TEM analysis of the Mn supported nano-catalyst

In another evaluation, the morphology and size of the Mn supported nano-catalyst were determined by SEM and TEM images (Fig. 4–5). The spherical shape of the Fe₃O₄@SiO₂@CPTMS@MBOL@Mn is conceived through the uniform nanometer-sized particles. In the SEM images, formation of sintered grains with the 35–47 nm size range was apparent. The core–shell structure of nano catalyst could be observed via TEM images. However, magneto static interactions of the particles could be the reason of some particle aggregations. At an exact scrutiny, according to distribution histograms (Fig. 6), the average sizes of the nanoparticles is anticipated between 19.1 and 29.7 nm.

2.1.6 Thermal properties of the Mn supported nano-catalyst

The thermo-gravimetric analysis shows the thermal stability and decomposition behavior of the Mn supported nano-catalyst beyond heating (Fig. 6). As observed there are about four weight loss stages for the catalyst in the ranges of 100, 185, 300, and 360 ᵒC, respectively. The initial weight reduction at about 100 ᵒC probably corresponds to the residual water, the second weight loss at about 180 ᵒC is possibly attributed to the thermal decomposition of the complex, the third weight loss at about 300 ᵒC is attributed to the thermal decomposition of the two CPTMS and MBOL ligands, and the fourth weight reduction at about 360 ᵒC is probably resulted from the de-coating of Fe₃O₄.

2.1.7 VSM analysis of the Mn supported nano-catalyst

Due to comparison of magnetic properties, the VSM analysis was performed for the five steps of preparing including A) Fe₃O₄ MNPs, B) Fe₃O₄@SiO₂, C) Fe₃O₄@ SiO₂-CPTMS, D) Fe₃O₄@SiO₂@CPTMS@MBOL and E) Fe₃O₄@SiO₂@CPTMS@MBOL@Mn (Fig. 7). Generally, all five steps of formation show magnetic possessions and a clear decrease from A to E (65, 35, 30, 10 and 4.35 emu/g, respectively) can be observed. In fact the dipolar–dipolar interactions reduce between the magnetic nanoparticles due to coating of Fe₃O₄ MNPs via different layers and complexation.

3.1 General

All chemicals (starting materials, reagents, solvents, etc) were acquired from the chemical companies and used in the absence of additionally purification.

3.2 Preparation of the Mn supported nano-catalyst

The Mn supported nano-catalyst was prepared according to the procedure described.³²

3.3 General Procedure for the synthesis of indazolophthalazinetriones

Phthalhydrazide (0.162 g, 1.0 mmole), dimedone (0.140 g, 1.0 mmole), an aldehyde derivative (1.0 mmole) and the Mn supported nano-catalyst (20 mg) were mixed in ethanol (5 mL), stirred and heated at reflux condition in appropriate times which depends on the substrate (Table 2), and completion of the reaction was monitored with TLC. After cooling, the Mn supported nano-catalyst was separated by a super magnet, H₂O (10 mL) added, and a white precipitate filtered and recrystallized in EtOH.

3.4 Optimization

To obtain the best result, effects of different conditions were investigated for this reaction. The one-pot three-component condensations of phthalhydrazide (1.0 mmole), 4-methylbenz-aldehyde (1.0 mmole) and dimedone (1.0 mmole) was chosen as a model reaction in different reaction conditions (amount of the catalyst temperature and solvent). The best result was achieved with 1.0 mmole of 1:1:1 of benzaldehyde: dimedone: phthalhydrazide in presence of 20 mg of the Mn supported nano-catalyst in EtOH at reflux condition (Table 1, entry 5).

Table 1

Optimization of the reaction conditions
Entry	Solvent	Catalyst (mg)	Temperature (˚C)	Time (min)	Yield (%)
1	EtOH/H₂O	10	80	15	71
2	EtOH/H₂O	20	80	15	82
3	EtOH/H₂O	30	80	15	74
4	EtOH/H₂O	40	80	15	74
5	EtOH	20	80	15	90
6	H₂O	20	80	15	76
7	Toluene	20	80	15	53
8	DMF	20	80	15	49
9	EtOH	20	60	15	72
10	EtOH	20	40	15	37
11	EtOH	20	rt	15	21

Also, two additional reactions were performed under the optimum conditions as below:

1. The synthesis of indazolophthalazinetriones carried out in the absence of Fe₃O₄@SiO₂@CPTMS@MBOL@Mn: The reaction efficiency was very low (trace).

2. The reaction was done in the presence of (Fe₃O₄@SiO₂@CPTMS@MBOL) and no product was observed.

3.5 Synthesis of diverse indazolophthalazinetriones (2a-j)

According to the optimization of model reaction, different indazolophthalazinetriones (2a-j) were synthesized from the one pot three-component condensation reaction of aldehydes, dimedone and phthalhydrazide in EtOH at reflux conditions in attendance of the Mn supported nano-catalyst with good to excellent yields in fast reaction times (Table 2).

3.6 Characterization of the products

All indazolophthalazinetriones were characterized and recognized by considering to their physical and spectroscopic analysis and comparing the reported in the literature. The structures of all products were confirmmed via their IR and NMR spectra (Supplementary data).

3,3-Dimethyl-13-phenyl-3,4-dihydro-1H-indazolo[2,1,b]phthalazine-1,6,11(2H,13H)-trione (2a): mp 202–206°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2953, 1663; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.80–8.37 (m, 4H), 7.26 (m, 5H), 6.45 (s, 1H), 3.30 (d ,2H, CH₂), 2.33 (s, 2H, CH₂), 1.22 (s, 6H, 2CH₃). ¹³C NMR (75 MHz, CDCl₃): 28.7, 34.7, 38, 5, 65, 77.5, 118, 127, 127, 127.7, 128, 128.6, 128.7, 128.8, 128.9, 129, 133.5, 134.5, 136.3, 150.8, 154.2, 156, 192.

13-(4-Chlorophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[2,1-b]phthalazine-1,6,11(2H,13H)-trione (2b): mp 260–263°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2957, 1660; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.81–8.41 (m, 4H), 7.32 (m, 4H), 6.41 (s, 1H), 3.30 (d, 2H, CH₂), 2.34 (s, 2H, CH₂), 1.21 (s, 6H, 2CH₃). ¹³C NMR (75 MHz, CDCl₃): 28.5, 34.4, 38, 50, 61.3, 77, 118, 127.7, 128.2, 129.2, 134, 151, 154.3, 192.

13-(4-Bromophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[2,1-b]phthalazine-1,6,11(2H,13H)-trione (2c): mp 256–259°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2959, 1687, 1654; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.86–8.39 (m, 4H), 7.23–7.35 (m, 4H), 6.70 (s, 1H), 3.23–3.45 (d, 2H, CH₂), 2.34 (s, 2H, CH₂), 1.23 (s, 6H, 2CH₃).

3,3-Dimethyl-13-(3-nitrophenyl)-3,4-dihydro-1H-indazolo[2,1,b]phthalazine-1,6,11(2H,13H)-trione (2d): mp 267–270°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2962, 1661; ¹H NMR (300 MHz, CDCl₃): δ_H = 7.87–8.40 (m, 4H), 6.52–7.59 (m, 4H), 6.52 (s, 1H), 3.24–3.47 (dd, 2H, CH₂), 2.35 (s, 2H, CH₂), 1.22 (s, 6H, 2CH₃). ¹³C NMR (75 MHz, CDCl₃): 27.3, 28.4, 28.6, 34.7, 38, 50.8, 64, 76.5, 77, 117, 121.5, 123.7, 127.7, 128.2, 128.6, 129, 129.6, 134, 134.2, 134.7, 138.6, 148.5, 151.8, 154.6, 156, 192.

13-(2,4-Dichlorophenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[2,1-b]phthalazine-1,6,11-(2H, 13H)-trione (2e): mp 219–222°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2964, 2940, 1663; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.75–8.38 (m, 4H), 7.13–7.26 (m, 3H), 6.6 (s, 1H), 3.3 (d, 2H, CH₂), 2.33 (s, 2H, CH₂), 1.22 (s, 6H, 2CH₃). ¹³C NMR (75 MHz, CDCl₃): 28.8, 34.6, 38, 50.8, 63.5, 77, 127.6, 127.7, 128, 128.6, 129, 130.4, 131.7, 133.2, 133.7, 134.6, 135, 152, 154.3, 156, 192.

3,4-Dihydro-3,3-dimethyl-13-(4-methylphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (2f): mp 224–227°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2924, 1687, 1655; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.77–8.28 (m, 4H), 7.17–7.35 (m, 4H), 6.4 (s, 1H), 3.3 (d, 2H, CH₂), 2.29–2.32 (m, 5H), 1.21 (s, 6H, 2CH₃).

13-(4-Methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-indazolo[2,1-b]phthalazine-1,6,11-(2H, 13H)-trione (2g): mp 219–221°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2956, 1664; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.92–8.24 (m, 4H), 7.54–7.82 (m, 4H), 6.5 (s, 1H), 3.77 (s, OCH₃) 3.33 (d, 2H, CH₂), 2.33 (s, 2H, CH₂), 1.2 (s, 6H, 2CH₃).

3,4-Dihydro-3,3-dimethyl-13-(2-eylnaphtalene)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (2h): mp 249–251°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2967, 1681, 1664; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.45–8.38 (m, 11H), 6.62 (s, 1H), 3.24–3.5 (dd, 2H), 2.33 (s, 2H), 1.22(s, 6H). ¹³C NMR (75 MHz, CDCl₃): 118.6, 124, 126.2, 126.3, 126.8, 127.7, 128, 128.2, 128.7, 129, 133.2, 133.4, 133.5, 133.6, 134.5, 150.8, 156, 192.

13-Ethyl-3,3-dimethyl-3,4-dihydro-1H-indazolo[2,1-b]phthalazine-1,6,11(2H,13H)-trione (2i): mp 264–267°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2962, 2931, 1652; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.81–8.35 (m, 4H), 5.69 (m, 1H), 3.16 (d, 2H, CH₂), 2.16–2.37 (m, 4H, 2CH₂), 1.19 (s, 6H, 2CH₃), 0.65–0.82 (t, 3H, CH₃).

3,4-Dihydro-3,3-dimethyl-13-(4-thiomethylphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione (2j): mp 228–230°C; FT-IR (KBr, cm^− 1): The characteristic IR peaks: 3100, 3000, 2959, 2978, 1663; ¹H NMR (90 MHz, CDCl₃): δ_H = 7.84–8.37 (m, 4H), 7.1–7.35 (m, 4H), 6.4 (s, 1H), 3.21–3.45 (d, 2H, CH₂), 2.42 (s, 3H), 2.34 (s, 2H), 1.2 (s, 6H).

3.7 The plausible mechanism

A persuasive mechanism for the synthesis of diverse phthalazine-triones is illustrated as below. The reaction is followed by mixture of regents in EtOH at reflux conditions in the presence of the Mn supported nano-catalyst (Scheme 3).

The suggested mechanism is presumably in accordance of the Lewis acidity of the Mn supported nano-catalyst by connecting to the carbonyl group to simplify the nucleophilic attack of the enolic form of dimedone (Knoevenagel condensation) to aldehyde to form the intermediate with the subsequent deletion of water, the nucleophilic attack of phthalhydrazide, deletion of water, and the final cyclization to get the product.

3.8 Comparison of Catalytic activity

Table 3 shows the comparison of the previous procedures (entries 1–9) used for the synthesis of 3,4-Dihydro-3,3-dimethyl-13-(4-methylphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trionewith our used method (entry 10). In general, each procedure includes some advantages that by focusing on the pervious routes we could declare this method could accelerate the process of reaction and be useful and efficient as well.

Table 3

Comparison of the Mn supported nano-catalyst capability with the other catalysts in synthesis of 3,4-dihydro-3,3-mimethyl-13-(4-methylphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione
Entry	Catalyst	Solvent^a	T^b (°C)	Time (min)	Yield (%)	Ref.
1	MNPs-guanidine (0.03 g)	SF	70	40	90	34
2	β-Cyclodextrin	H₂O	80	30	86	35
3	[Simp]₃PW₁₂O₄₀ (0.03 g)	SF	100	60	66	36
4	PTA@Fe₃O₄/EN-MIL-101 (0.02 g)	SF	100	60	70	37
5	Fe₃O₄@Silica sulfuric acid (0.075 g)	SF	100	40	86	38
6	MNPs-PSA (0.03)	SF	100	30	90	39
7	H₂SO₄ (0.015 %mmole) in EtOH/H₂O	EtOH	Reflux	30	86	40
8	MnFe₂O₄@SiO₂@NH-NH₂-PTA (0.03 g)	SF	80	30	87	41
9	CAN (5 %mol)	PEG	50	150	94	42
10	Fe₃O₄@SiO₂@CPTMS@MBOL@Mn (0.02 g)	EtOH	Reflux	15	90	PW^c
^aSF = Solvent-free, ^bT = temperature, ^cPW = present work

3.9 Reusability of the Mn supported nano-catalyst

To investigate the recyclability of the Mn supported nano-catalyst for environmental and commercial applications, it was tested with the model reaction, and found that it is relatively capable even after five runs and its activity was almost similar to the fresh one (90, 90, 88, 87, and 84%) respectively (Fig. 8). The stability of the Mn supported nano-catalyst even after the 5th run was inspected by FT-IR and SEM techniques (Fig. 9–10).

3.10 Antibacterial properties

The antibacterial properties of the Mn supported nano-catalyst were studied against a number of gram-positive and gram-negative bacterial strains, and DMSO was used as a blank (Table 4). The catalyst inhibited the growth of bacterial strains, producing a zone of inhibition of diameter 5–30 mm. The Mn supported nano-catalyst was even more effective against Serratia marcescens in gram-negative bacteria than the standard tetracycline antibiotic. Since the comparison of the size of inhibition zones is generally not reliable, the MIC value of the compound was also determined. The results indicated that the MIC value of the Mn supported nano-catalyst against the tested organisms was about 8 mg/mL. The MIC value of standard tetracycline antibiotic is about 8 mg/mL.

Table 4 Antibacterial activity of Mn supported nano catalyst that was expressed as diameter of inhabitation zone (mm) and minimum inhibitory concentration (MIC)

Microorganisms

Standard

Blank

Zone of inhabitation (mm)

MIC (mg/mL)

Tetracycline (10 mg/mL)

DMSO

the Mn catalyst

Gram (+)

Bacillus thuringiensis

Bacillus cereus

Staphylococcus aureus

Gram (^_)

Pseudomonas aeruginosa Serratia marcescens

Escherichia coli

Klebsiella pneumoniae

In conclusion, we were successful to synthesize a novel Mn nano-catalyst supported on magnetic iron oxide functionalized with mercaptobenzoxazole as an appropriate surface for synthesis of 2H-Indazolo[1,2-b]phthalazine-triones from the one pot three-component condensation reaction of aldehydes, dimedone and phthalhydrazide in refluxed ethanol in fine yields and short reaction times. In fact iron oxide nanoparticles through the noticeable properties such as small size, high magne-tism and low toxicity would be a proper methods for chemistry synthesis. Also we inspected the antibacterial properties of Mn nano catalyst against a number of gram-positive and gram-negative bacterial strains and determined the nano catalyst would be more effective against Serratia marcescens in gram-negative bacteria than the standard tetracycline antibiotic. Environmental issues revealed that the Mn nano catalyst would be used for five runs without significant loss of the catalytic activity.

Acknowledgement

Gratefully this project was financially supported by Bu-Ali Sina University.

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A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity

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Abstract

Figures

1 Introduction

2 Results And Discussion

2.1 Characterization of the Mn supported nano-catalyst

2.1.1 ICP analysis of the Mn supported nano-catalyst

2.1.2 FT-IR spectroscopy of the Mn supported nano-catalyst

2.1.3 XRD analysis of the Mn supported nano-catalyst

2.1.4 EDX analysis of the Mn supported nano-catalyst

2.1.5 SEM and TEM analysis of the Mn supported nano-catalyst

2.1.6 Thermal properties of the Mn supported nano-catalyst

2.1.7 VSM analysis of the Mn supported nano-catalyst

3 Experimental

3.1 General

3.2 Preparation of the Mn supported nano-catalyst

3.3 General Procedure for the synthesis of indazolophthalazinetriones

3.4 Optimization

3.5 Synthesis of diverse indazolophthalazinetriones (2a-j)

3.6 Characterization of the products

3.7 The plausible mechanism

3.8 Comparison of Catalytic activity

3.9 Reusability of the Mn supported nano-catalyst

3.10 Antibacterial properties

4 Conclusion

Declarations

References

Tables

Supplementary Files

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