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[ CAS No. 70458-96-7 ] {[proInfo.proName]}

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Chemical Structure| 70458-96-7
Chemical Structure| 70458-96-7
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Shabbir, Sanya ; Hadi, Abdullah ; Jabeen, Nusrat , et al. DOI:

Abstract: Antibiotics are the major therapeutic arsenal against bacterial infections. Yet, beneath this medical triumph lies an under investigated challenge of the potential teratological and toxicological impacts associated with the use of antibiotics. In the present study, we have explored the teratogenic potential of five commonly used antibiotics (streptomycin, metronidazole, , doxycycline and norfloxacin) on Drosophila melanogaster Oregon-R strain. Except , all other tested antibiotics significantly delayed the onset of pupariation. Consistently, metronidazole, doxycycline and resulted in statistically significant drops in egg-toadult viability and adversely affected egg-to-pupa transition. In comparison, embryonic exposure of streptomycin impeded pupa-to-fly transition. All tested antibiotics induced morphological defects in antenna, wings, proboscis, eye, head, thorax, haltere and abdomen. Interestingly, developmental exposure of antibiotics resulted in statistically significant decrease in the lifespan of both male and female flies. This suggests an increased incidence of teratogenic faults at the systemic level, which are otherwise not manifested morphologically, due to the exposure of tested antibiotics during development. Taken together, our data show that developmental exposure of antibiotics may induce varying degrees of teratogenicity in D. melanogaster. Given the genomic homology and conservation of major molecular pathways that underpin development in humans and D. melanogaster, the findings do hold translational potential.

Keywords: Antibiotics ; Drosophila melanogaster ; Development ; Teratogenicity ; Lifespan

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Product Details of [ 70458-96-7 ]

CAS No. :70458-96-7 MDL No. :MFCD00079532
Formula : C16H18FN3O3 Boiling Point : -
Linear Structure Formula :C4N2H9C6H2FC3HON(C2H5)COOH InChI Key :OGJPXUAPXNRGGI-UHFFFAOYSA-N
M.W : 319.33 Pubchem ID :4539
Synonyms :
MK-366
Chemical Name :1-Ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

Safety of [ 70458-96-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 70458-96-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 70458-96-7 ]

[ 70458-96-7 ] Synthesis Path-Downstream   1~4

  • 1
  • copper(II) choride dihydrate [ No CAS ]
  • [ 70458-96-7 ]
  • [ 2848-01-3 ]
  • C31H31CuFN3O5P*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.7% With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux; General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ～6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 .
  • 2
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 70458-96-7 ]
  • [ 2848-01-3 ]
  • C31H31FN3O6PV [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.77% In methanol; for 10h;pH Ca. 6.8;Reflux; General procedure: To a hot solution of VOSO4 (2) (5 mmol) in MeOH(25.0 mL), previously prepared methanolic solution ofligand 3-(diphenylphosphino)-propionic acid (1) (5 mmol)was added, with constant stirring. Then, alkaline methanolicsolution of ciprofloxacin (5 mmol) was added. The pH of thereaction mixture was adjusted to*6.8. The resulting greensolution was refluxed for 10 h and concentrated under vacuum.Upon addition of Et2O, a green solid precipitate wasobtained, which was collected by filtration, washed withEt2O and dried in vacuo (Gajera et al., 2015). General synthesisof complexes is shown in Scheme 1. Yield: 62.61 %.M.P:[300. Anal. Calcd (%). for C32H33FN3O6PV: C, 58.54;H, 5.07; N, 6.40; V, 7.76. Found (%): C, 58.24; H, 4.76; N,6.89; V, 7.26. UV-VIS in DMSO [kmax/nm (e/M-1 cm-1)]:421 (23,729), 584 (17,100), 807 (12,391). FT-IR: tmax(cm-1) m(C=O)pyridone 1628, m(CO2)asym 1586, m(CO2)-sym 1384, m = m(CO2)asym-m(CO2)sym = 202, m(V=O)952, m(M-O) 513 cm-1. ESI-MS (m/z):654.62 [M?].
  • 3
  • [ 4876-10-2 ]
  • [ 70458-96-7 ]
  • 1-ethyl-6-fluoro-7-(4-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.9% Norfioxacin (3.1; 1 g, 3.13 mmol, 1 eq) was added to a 1:1 mix of acetonitrile and water(so mL total). After stirring for s minutes, potassium carbonate (1298 mg, 9.39 mmol,3 eq) was added and the mixture stirred for a further s minutes. Once fully dissolved, 4- (bromomethyl)quinolin-2(1H)-one (708 mg, 2.97 mmol, 0.95 eq) was added slowly over the course of 1 hour and the mixture subsequently stirred for 24 hours. Upon completion, extraction using dichloromethane (2x100 mL), using a 1M solution of citric acid to neutralise the aqueous phase, resulted in formation of a white precipitate. The precipitate was filtered, washed with distilled water (100 mL) and methanol (100 mL)then re-dissolved in excess DMSO. Purification was achieved using an SCX-2 catch and release cartridge (see Solid Phase Extraction method) to afford compound 3.14 (1.26 g, 88.9 percent yield) as an off white solid. LC-MS Retention time 2.87 minutes, found 477.0 [M+H] calculated for C26H25FN404477.51 [M+H].
  • 4
  • [ 71831-21-5 ]
  • [ 70458-96-7 ]
  • 1-ethyl-6-fluoro-7-(4-(4-(hydroxymethyl)benzyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.1% Norfioxacin (3.1; 100 mg, 0.31 mmol, 1 eq) was added to a 1:1 mix of acetonitrile and distilled water (s mL total). After stirring for s minutes, potassium carbonate (130 mg, 0.94 mmol, 3 eq) was added and the mixture stirred for a further minutes. Once fully dissolved, <strong>[71831-21-5](4-(bromomethyl)phenyl)methanol</strong> (63 mg, 0.31 mmol, 1 eq) was addedslowly over the course of 1 hour and the mixture subsequently stirred for 7 days. Upon completion, the product was extracted with dichloromethane (2x20 mL) using a 1M solution of citric acid to neutralise the aqueous phase. Combined organic fractions were washed with distilled water (20 mL) and dried over MgSO4, filtered and concentrated in vacuo to give the crude product. Purification was achieved using an SCX-2 catch andrelease cartridge (see Solid Phase Extraction method) to afford (133.70 mg, 97.1 percent yield) 3.40 as an off white solid. 1H NMR (400 MHz, CDC13) 6 15.13 (br. s., 1H), 8.64 (s, 1H), 7.98 (d, J = 13.09 Hz, 1H),7.35 (s, 4H), 6.82 (d, J = 6.80 Hz, 1H), 4.70 (s, 2H), 4.31 (q, J = 7.13 Hz, 2H), 3.59 (s,2H), 3.30 - 3.36 (m, 4H), 2.64 - 2.70 (m, 4H), i.6 (t, J = 7.18 Hz, 3H); 13C NMR (ioo MHz, CDC13) 6 176.9, 167.3, 152.3, 147.1, 146.3, 146.2, 140.1, 137.1, 136.9, 129.4 (2C), 127.1 (2C), 120.4, 120.3, 112.7, 112.5, 108.2, 103.8, 6.o, 62.6, 53.5, 52.6 (2C), 49.9, 49.8, 14.4; LC-MS Retention time 5.03 minutes, Found 440.1 [M+H] calculated forC24H26FN304 440.49 [M+H]
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Chemical Structure| 68077-27-0

A268468[ 68077-27-0 ]

Norfloxacin hydrochloride

Reason: Free-salt

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