Structural, optical and antimicrobial studies of 3β-acetoxycholest-5-ene, 3β-acetoxy-6-nitrocholest-5-ene and newly synthesized steroidal pyrazolones

Peer review under responsibility of Taibah University

Figures & data

Table 2 The XRD parameters of the nano compounds 7–9 prepared in this study.

Parameters	7	8	9
Formula	C32H51N3O3	C30H48ClN3O	C30H49N3O
Molecular weight (g mol^−1)	525	499/501	467
Melting point (°C)	145 °C	131 °C	119 °C
Crystal system	Hexagonal	Hexagonal	Orthorhombic
Method	Powder	Powder	Powder
Cell parameters	a = 4.9168	a = 4.9168	9.105869
	b = 4.9168	b = 4.9168	7.712702
	c = 5.4089	c = 5.4089	7.600149
	α = 90	α = 90	90
	β = 90	β = 90	90
	γ = 120	γ = 120	90
2θ min–max	20–42.8	20–80	20–80
Lattice type	P	P	P

Table 3 The zones of inhibition of nanocompounds 2 and 3 with respect to positive and negative control in antibacterial activity.

	Zone of inhibition (mm)
Compounds	S. aureus	S. pyogenes	P. aeruginosa	E. coli
2	10.1 ± 0.3	12.2 ± 0.2	13.3 ± 0.3	9.5 ± 0.1
3	14.5 ± 0.4	12.6 ± 0.5	13.5 ± 0.5	11.2 ± 0.5
7	17.3 ± 0.3	19.5 ± 0.1	16.1 ± 0.3	14.9 ± 0.2
8	15.8 ± 0.4	13.7 ± 0.5	14.6 ± 0.5	15.4 ± 0.5
9	17.3 ± 0.6	18.2 ± 0.2	15.4 ± 0.4	13.9 ± 0.6
Chloramphenicol	20.6 ± 0.5	21.5 ± 0.4	22.2 ± 0.8	19.0 ± 0.2
DMSO	–	–	–	–

Bold numbers represent higher zone of inhibition values.

Table 4 The zones of inhibition of nanocompounds 2 and 3 with respect to positive and negative control in antifungal activity.

	Zone of inhibition (mm)
Compounds	C. albicans	T. mentagrophytes	P. marneffei	A. fumigatus
2	13.1 ± 0.2	10.2 ± 0.4	8.1 ± 0.1	9.4 ± 0.2
3	11.1 ± 0.3	13.2 ± 0.4	11.5 ± 0.2	13.8 ± 0.5
7	26.2 ± 0.5	22.1 ± 0.5	14.2 ± 0.2	13.3 ± 0.4
8	23.6 ± 0.6	21.6 ± 0.4	13.9 ± 0.5	16.2 ± 0.2
9	24.2 ± 0.2	23.2 ± 0.6	16.2 ± 0.3	15.1 ± 0.2
Nystatin	29.0 ± 0.5	29.0 ± 0.5	19.5 ± 0.5	19.5 ± 0.5
DMSO	–	–	–	–

Bold numbers represent higher zone of inhibition values.

Scheme 1 Schematic representation of the formation of nano steroids 2 and 3.

Scheme 2 Schematic representation of the formation of steroidal pyrazolones.

Scheme 3 Mechanism for the formation of steroidal pyrazolones.

Fig. 1 The typical XRD pattern shown by the nano compounds 1–3 and 7–9 at room temperature.

Fig. 2 The graph shown particle size analysis of nano steroid 3 and 7–9.

Table 1 The XRD parameters of the nano compounds 2 and 3 prepared in this study.

Parameters	2	3
Formula	C29H48O2	C29H47NO4
Molecular weight (g mol^−1)	428.70	473.69
Melting point (°C)	114	104
Crystal system	Monoclinic	Tetragonal
Method	Powder	Powder
Cell parameters	a = 12.1212	a = 7.3841
	b = 8.1864	b = 7.3841
	c = 6.9731	c = 15.8426
	α = 90.00	α = 90.000
	β = 103.2028	β = 90.000
	γ = 90.000	γ = 90.000
2θ min–max	21.706–76.835	20.357–76.829
crystal size	37.03 nm	1.901 nm
Lattice type	p	p

Fig. 3 SEM images showing surface morphology and crystalline nature of compound 2, 3 and 7–9.

Fig. 4 Showing the UV–vis absorption spectra of nano steroids 1–3 and 7–9.

Fig. 5 The fluorescence intensity curves of nano steroids 2 and 3.

Fig. 6 Graphs showing the band gap energy (Eg) of nano steroids 2, 3, 7 and 8.

Fig. 7 The characteristic absorption peaks in infrared spectra (IR) of nano steroids 2 and 3.

Fig. 8 Antimicrobial activity of 3 against P. Aeruginosa (a), S. aureus (b) and A. fumigatus (c) Antimicrobial activity of 7 against S. Pyogenes (d) and C. Albicans (e).

Fig. 9 The graphical representation of antibacterial (a) and antifungal (b) activity of nano compounds 2, 3 and 7–9 with positive controls.