[ CAS No. 111-24-0 ] {[proInfo.proName]}

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Quality Control of [ 111-24-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 111-24-0 ]

SDS Specification

Alternatived Products of [ 111-24-0 ]

Product Citations Expand+

Inhibiting NOXO1 and CYBA binding to reduce NADPH oxidase I dependent ROS damage in skin explants

Senevirathne, Prasadini ; Sterling, Alyssa ; Anne Refaei, Mary , et al. Results Chem.,2023,6,101213. DOI: 10.1016/j.rechem.2023.101213

Abstract: NADPH oxidases (NOXs) are newly identified enzymes that generate intracellular reactive oxygen species (ROS) in skin cells. Recent studies demonstrated that NOX1 holoenzyme is expressed in human keratinocytes and melanocytes, which are implicated in skin photo-carcinogenesis due to the high amounts of ROS produced. Holoenzyme activation requires a ternary complex comprised of NOX1, cytochrome B alpha chain (CYBA), and cytoplasmic NADPH Oxidase Organizer 1 (NOXO1) to properly form. By inhibiting this assembly process, an opportunity for reducing the production of catalytic ROS is possible, especially during high ROS conditions that occur under prolonged UV exposure. We designed a series of small mols. and evaluated their inhibitory effects on NOXO2 using in-silico docking methods in the 1WLP crystal structure. We show that the NOX_inh_5 inhibitor was successful in a variety of experiments using primary skin models from various skin tones. NOX_inh_5 proved to be non-cytotoxic while also improving the viability of primary human skin primary cells under UV exposure. Biophys. studies with NOX_inh_5 using an Isothermal calorimetric (ITC) binding and heteronuclear single quantum coherence (HSQC-NMR) exhibited inhibition of complex formation between NOXO2 and CYBA. Authentic human skin explants, treated with and without NOX_inh_5 and UV exposure, decreased p53 stabilization and decreased UV-induced DNA damage as quantified through cyclobutane dimer formation.

Keywords: Reactive oxygen species ; Apocynin ; UV ; Melanoma ; Sunscreen ; NOXO1 ; CYBA

Purchased from AmBeed: 1007-16-5 ; 111-24-0 ; 583-55-1 ; 455-85-6

Development of reactive oxygen species (ROS) inhibitors and prodrugs for multiple applications

Senevirathne, Priyangika Prasadini ; University of Cincinnati,2022.

Abstract: Reactive oxygen species are a group of highly reactive oxygen-containing entities that are important at a cellular level for multiple biological processes. Low concentrations of ROS can be beneficial as powerful signaling molecules in those biological processes, although excessive concentrations can promote high levels of DNA damage and a variety of diseases such as skin cancer. A newly identified intracellular ROS production source in skin cells is NADPH oxidases. Out of the NOX enzyme family, the NOX1 holoenzyme is most abundantly expressed in the human keratinocyte cells. UV radiation can trigger the activation of NOX1 isoforms which stimulate the assembling of member CYBA and the cytoplasmic protein NOXO1. Inhibition of these enzymes represents a catalytic approach toward reducing ROS for the prevention of ROS inducible diseases. Key disease states include melanoma induced by UV exposure. The first half of the dissertation focuses on investigating new small molecule inhibitors of a key NOX1 holoenzyme to address these challenges. We designed a series of molecules by optimizing the structure of diapocynin and evaluated by in-silico docking methods to determine the binding affinity with NOXO1 cytoplasmic protein (1WLP crystal structure). And have synthesized the series of target molecules for the structure-activity relationship studies. In the first section of the project, we discovered that inhibitor NOX_inh_5 was not cytotoxic, but instead improved the viability of human primary cells from UV exposure, decreased the cellular stress in human skin through the p53 pathway, and reduced the UV-induced DNA damage as monitored by quantification of cyclobutane dimer formation after UV exposure. Then, we characterized the inhibition potential of NOX_inh_5 by using an Isothermal calorimetric (ITC) binding assay and heteronuclear single quantum coherence (HSQC) technique and revealed that the candidate iii molecule can prevent the complex formation of NOXO1 and CYBA membrane protein. In the second section of the project, we did a structure-activity relationship study for the NOX_inh_5 small molecule to optimize the biological characteristics. The last section of the dissertation discussed the development of ROS sensible prodrug to combat the opioid overdose crisis. Here we used oxidative stress conditions caused by opioid overdose to activate the prodrug. Even though opioid antagonist naloxone has a high affinity to bind with opioid receptors to block opioid-induced activation, it is metabolically unstable and has a short half-life of around 33 min. We developed a peroxide-induced prodrug to overcome this issue that can release a steady stream of naloxone. This allows the concentration of naloxone to remain high for longer periods.

Purchased from AmBeed: 1007-16-5 ; 111-24-0 ; 14221-01-3 ; 99769-19-4 ; 351422-73-6 ; 158407-04-6 ; 1462-37-9 ; 583-61-9 ; 13965-03-2 ; 455-85-6 ; 148893-10-1

Product Details of [ 111-24-0 ]

CAS No. :	111-24-0	MDL No. :	MFCD00000268
Formula :	C₅H₁₀Br₂	Boiling Point :	-
Linear Structure Formula :	CH₂(C₂H₄Br)₂	InChI Key :	IBODDUNKEPPBKW-UHFFFAOYSA-N
M.W :	229.94	Pubchem ID :	8100
Synonyms :

Calculated chemistry of [ 111-24-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.89
TPSA :	0.0 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	2.82
Log Po/w (WLOGP) :	2.95
Log Po/w (MLOGP) :	3.29
Log Po/w (SILICOS-IT) :	2.68
Consensus Log Po/w :	2.85

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.78
Solubility :	0.383 mg/ml ; 0.00167 mol/l
Class :	Soluble
Log S (Ali) :	-2.48
Solubility :	0.766 mg/ml ; 0.00333 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.62
Solubility :	0.0558 mg/ml ; 0.000243 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.56

Safety of [ 111-24-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P210-P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319	Packing Group:	N/A
GHS Pictogram:

Applications of [ 111-24-0 ]

1,5-Dibromopentane (CAS: 111-24-0) can be used in the preparation of ETC-1002 (CAS: 738606-46-7). Bempedoic acid is a first-in-class adenosine triphosphate-citrate lyase (ACL) inhibitor.

Application In Synthesis of [ 111-24-0 ]

* 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.

Upstream synthesis route of [ 111-24-0 ]
Downstream synthetic route of [ 111-24-0 ]

[ 111-24-0 ] Synthesis Path-Upstream 1~2

1
[ 111-24-0 ]
[ 100-33-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1252 - 1257
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 2, p. 592 - 608

2
[ 111-24-0 ]
[ 112-18-5 ]
[ 18464-25-0 ]

Reference： [1] Molecules, 2011, vol. 16, # 1, p. 319 - 335
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5824 - 5828
[3] Pharmaceutical Chemistry Journal, 1968, # 5, p. 247 - 250[4] Khimiko-Farmatsevticheskii Zhurnal, 1968, # 5, p. 15 - 18

[ 111-24-0 ] Synthesis Path-Downstream 1~10

1
[ 111-24-0 ]
[ 619-60-3 ]
[ 111293-74-4 ]

Reference： [1]Patent: DE1019317,1954,

2
[ 111-24-0 ]
[ 3743-22-4 ]
[ 111294-45-2 ]

Reference： [1]Patent: DE828550,1950,
DRP/DRBP Org.Chem.,

3
[ 111-24-0 ]
[ 407-97-6 ]

Reference： [1]Journal of Organic Chemistry,1950,vol. 15,p. 425,427

4
[ 2346-00-1 ]
[ 111-24-0 ]
[ 55089-26-4 ]

Reference： [1]Journal of Organic Chemistry,1975,vol. 40,p. 2021 - 2025

5
Wang-benzaldehyde resin, imine with glycine ethyl ester [ No CAS ]
[ 111-24-0 ]
[ 63203-48-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 3188 - 3193

6
[ 111-24-0 ]
[ 84-67-3 ]
[ 1221066-32-5 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 1096 - 1110

7
[ 111-24-0 ]
[ 161798-01-2 ]
C₁₉H₂₂BrNO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 75℃;	General procedure: Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate 2 (1.0 mmol), dimethyl formamide (4 mL) as a solvent media and potassium carbonate (1.05 mmol)was taken in RBF and heated to 75°C for 15 to 20 min and then dibromoethane (2.0 mmol) solution in dimethylformamide (1 mL) was added and reaction continued for 4-5 hr. The completion of reaction was checked by TLC. Heating was stopped after the completion of reaction and reaction mixture was gradually cooled to RT. It was filtered and washed with dimethyl formamide (1 mL). The reaction mass was collected and poured onto water (20 mL), stirred for 30 min, filtered and washed with water. The product ethyl 2-(4-(2-bromoethoxy)-3-formylphenyl)-4-methylthiazole-5-carboxylate 5 was purified by recrystallization from IPA at RT.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2015,vol. 54B,p. 1005 - 1010

8
[ 111-24-0 ]
[ 61439-59-6 ]
1-benzyloxy-4-[2'-{(5''-bromopentyl)oxy}ethyl]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 5h;Inert atmosphere;	To a solution of <strong>[61439-59-6]2-(4-(benzyloxy)phenyl)ethanol</strong> (100.1 mg,0.44 mmol) in anhydrous DMF (5 mL) were added NaH (63.1 mg,2.50 mmol, 5.7 equiv.) and 1,5-dibromopentane (480 mL, 3.42 mmol,7.8 equiv.). The corresponding mixturewas stirred at rt and under Arfor 5 h.After that, itwas partitioned between 1:1 Et2OeH2O(30 mL);the aqueous phase was further extracted with Et2O (2x 15mL). Thecombined organic fractions were dried over Na2SO4, filtered andconcentrated to dryness. The residue was purified by column chromatography(cyclohexane/1:10 Et2Ocyclohexane). Yield:103.6 mg, 63%; Rf 0.82 (1:2 EtOAccyclohexane). 1H NMR(300 MHz, CDCl3) delta 7.39 (m, 5H, m, AreH), 7.15 (m, 2H, H-3, H-5), 6.92(m, 2H, H-2, H-6), 5.06 (s, 2H, Ph-CH2), 3.60 (t, 2H, JH,H 7.1 Hz, CH2),3.45 (t, 2H, JH,H 6.4 Hz, CH2), 3.40 (t, 2H, JH,H 6.8 Hz, CH2), 2.84 (t,2H, JH,H 7.1 Hz, CH2), 1.87 (quint, 2H, CH2), 1.60 (m, 2H, CH2), 1.49(m, 2H, CH2) ppm; 13CNMR(75.5 MHz, CDCl3) delta 157.4 (C-1),137.3 (C-10),131.5 (C-4),130.0,128.7,128.0,127.6 (Ar-C),114.9 (C-2, C-6), 72.2(C-200), 70.7, 70.1 (Ph-CH2O, C-100), 35.6, 33.9, 32.7 (CH2), 29.0 (C-200),25.1 (C-300) ppm; HRESI-MS calcd. for C20H2579BrNaO2 ([M+Na]+):399.0930, found: 399.0927.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 181

9
[ 111-24-0 ]
[ 7499-66-3 ]
ethyl 2-(1-(6-bromonaphthalen-2-yl)-1,4,5,6-tetrahydropyridin-3-yl)-3,3,3-trifluoropropanoate [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8543 - 8547

10
[ 111-24-0 ]
[ 7499-66-3 ]
1-(6-bromonaphthalen-2-yl)piperidine [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8543 - 8547

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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[ 111-24-0 ]

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[ CAS No. 111-24-0 ] {[proInfo.proName]}

Quality Control of [ 111-24-0 ]

Related Doc. of [ 111-24-0 ]

Product Citations Expand+

Product Details of [ 111-24-0 ]

Calculated chemistry of [ 111-24-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 111-24-0 ]

Applications of [ 111-24-0 ]

Application In Synthesis of [ 111-24-0 ]

[ 111-24-0 ] Synthesis Path-Upstream 1~2

[ 111-24-0 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 111-24-0 ]

Aliphatic Chain Hydrocarbons

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 111-24-0 ]