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Quality Control of [ 872-85-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 872-85-5 ]

Product Citations Expand+

Achieving Smart Photochromics Using Water-Processable, High-Contrast, Oxygen-Sensing, and Photoactuating Thiazolothiazole-Embedded Polymer Films

Tyler J. Adams ; Naz F. Tumpa ; Maithili Acharya , et al. ACS Appl. Opt. Mater.,2024,2(5):704-713. DOI: 10.1021/acsaom.4c00014

Abstract: Water-soluble dipyridinium thiazolo[5,4-d]thiazole (TTz) compounds are incorporated into inexpensive poly(vinyl alcohol) (PVA)/borax films and exhibit fast (<1 s), high-contrast photochromism, photofluorochromism, and oxygen sensing. Under illumination, the films change from clear/yellow TTz2+ to purple TTz?+ and then blue TTz0. The contrast and speed of the photochromism are dependent on the polymer matrix redox properties and the concentration of TTz2+. The photoreduced films exhibit strong, near-infrared light (1000–1500 nm) absorbances in addition to visible color changes. Spectroscopic ellipsometry was used to establish the complex dielectric function for the TTz2+ and TTz0 states. Incorporating non-photochromic dyes yields yellow-to-green and pink-to-purple photochromism. Additionally, when illuminated, reversible photoactuation occurs, causing mechanical contraction in the TTz-embedded films. The blue film returns to its colorless state via exposure to O2, making the films able to sense oxygen and leak direction for smart packaging. These films show potential for use in self-tinting smart windows, eyeglasses, displays, erasable memory devices, fiber optic communication, and oxygen sensing.

Keywords: photochromic ; photofluorochromic ; photoactuator ; thiazolothiazole ; oxygen sensor ; sensing ; green chemistry

Purchased from AmBeed: 872-85-5 ; 80-48-8 ; 79-40-3 ; 3779-42-8

SAR study of piperidine derivatives as inhibitors of 1,4-dihydroxy-2-naph- thoate isoprenyltransferase (MenA) from Mycobacterium tuberculosis

Berg, Kaja ; Hegde, Pooja ; Pujari, Venugopal , et al. Eur. J. Med. Chem.,2023,249,115125. DOI: 10.1016/j.ejmech.2023.115125 PubMed ID: 36682292

Abstract: The electron transport chain (ETC) in the cell membrane consists of a series of redox complexes that transfer electrons from electron donors to acceptors and couples this electron transfer with the transfer of protons (H+) across a membrane. This process generates proton motive force which is used to produce ATP and a myriad of other functions and is essential for the long-term survival of Mycobacterium tuberculosis (Mtb), the causative organism of tuberculosis (TB), under the hypoxic conditions present within infected granulomas. Menaquinone (MK), an important carrier molecule within the mycobacterial ETC, is synthesized de novo by a cluster of enzymes known as the classic/canonical MK biosynthetic pathway. MenA (1,4-dihydroxy-2-naphthoate prenyltransferase), the antepenultimate enzyme in this pathway, is a verified target for TB therapy. In this study, we explored structure-activity relationships of a previously discovered MenA inhibitor scaffold, seeking to improve potency and drug disposition properties. Focusing our campaign upon three molecular regions, we identified two novel inhibitors with potent activity against MenA and Mtb (IC50 = 13-22 μM, GIC50 = 8-10 μM). These analogs also displayed substantially improved pharmacokinetic parameters and potent synergy with other ETC-targeting agents, achieving nearly complete sterilization of Mtb in combination therapy within two weeks in vivo. These new inhibitors of MK biosynthesis present a promising new strategy to curb the continued spread of TB.

Keywords: 1,4-dihydroxy-2-naphthoate prenyltransferase ; MenA ; MenA inhibitors ; Menaquinone ; Mtb ; Mycobacterium tuberculosis ; Piperidine derivatives ; SAR

Purchased from AmBeed: 25952-53-8 ; class="">90719-32-7 ; class="">872-85-5 ; class="">6457-49-4 ; class="">3769-41-3 ; class="">10338-57-5 ; class="">135-19-3 ; class="">135-19-3 ; class="">28177-48-2 ; class="">22246-18-0 ; class="">122334-37-6 ; class="">91914-06-6 ; class="">10040-98-9 ; class="">161975-39-9 ; class="span_more span_less">150-76-5 ; class="span_more span_less">371-41-5 ; class="span_more span_less">63754-96-1 ; class="span_more span_less">288-32-4 ; class="span_more span_less">3380-34-5 ; class="span_more span_less">1677-46-9 ; class="span_more span_less">166815-96-9 ; class="span_more span_less">700-57-2 ; class="span_more span_less">1204-86-0 ; class="span_more span_less">21725-69-9 ; class="span_more span_less">367-12-4 ; class="span_more span_less">1003-29-8 ; class="span_more span_less">627-35-0 ; class="span_more span_less">27292-49-5 ; class="span_more span_less">104324-16-5 ; class="span_more span_less">123855-51-6 ; class="span_more span_less">4328-13-6 ; class="span_more span_less">875401-70-0 ; class="span_more span_less">405272-71-1 ; class="span_more span_less">63614-86-8 ; class="span_more span_less">1420942-13-7 ; class="span_more span_less">25952-53-8 ; class="span_more span_less">1420895-21-1 ; class="span_more span_less">1078-18-8 ; class="span_more span_less">32363-45-4 ; class="span_more span_less">69564-68-7 ; class="span_more span_less">31519-22-9 ; class="span_more span_less">22246-18-0 ; class="span_more span_less">189618-33-5 ; class="span_more span_less">180847-24-9 ; class="span_more span_less">6264-98-8 ; class="span_more span_less">946680-75-7 ; class="span_more span_less">63608-38-8 ; class="span_more span_less">713-68-8 ; class="span_more span_less">62810-39-3 ; class="span_more span_less">189618-32-4 ; class="span_more span_less">180847-23-8 ; class="span_more span_less">63608-31-1 ; class="span_more span_less">15789-05-6 ; class="span_more span_less">63712-27-6 ; class="span_more span_less">63608-33-3 ; class="span_more span_less">63608-35-5 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Product Details of [ 872-85-5 ]

CAS No. :	872-85-5	MDL No. :	MFCD00006425
Formula :	C₆H₅NO	Boiling Point :	-
Linear Structure Formula :	(COH)C₅NH₄	InChI Key :	BGUWFUQJCDRPTL-UHFFFAOYSA-N
M.W :	107.11	Pubchem ID :	13389
Synonyms :

Calculated chemistry of [ 872-85-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.62
TPSA :	29.96 ?2

Pharmacokinetics

GI absorption :	High
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) :	-6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.95
Log Po/w (XLOGP3) :	0.43
Log Po/w (WLOGP) :	0.89
Log Po/w (MLOGP) :	-0.23
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	0.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.26
Solubility :	5.83 mg/ml ; 0.0545 mol/l
Class :	Very soluble
Log S (Ali) :	-0.63
Solubility :	25.3 mg/ml ; 0.236 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.91
Solubility :	1.33 mg/ml ; 0.0124 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 872-85-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338-P337+P313	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 872-85-5 ]

* 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 [ 872-85-5 ]
Downstream synthetic route of [ 872-85-5 ]

[ 872-85-5 ] Synthesis Path-Upstream 1~1

1
[ 586-95-8 ]
[ 75-91-2 ]
[ 872-85-5 ]
[ 81660-73-3 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 4, p. 1467 - 1472

[ 872-85-5 ] Synthesis Path-Downstream 1~10

1
[ 872-85-5 ]
[ 57497-39-9 ]
(Z)-N-(pyridin-4-ylmethylidene)-tert-butylamine N-oxide [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 5569 - 5576
[2]Russian Chemical Bulletin,2002,vol. 51,p. 297 - 305
Izvestiya Akademi Nauk, Seriya Khimicheskaya,2002,p. 283 - 290

2
[ 872-85-5 ]
[ 162167-97-7 ]
C₁₇H₂₅N₃O₂ [ No CAS ]

Reference： [1]Patent: EP1243589,2002,A1 .Location in patent: Page 302

3
[ 872-85-5 ]
[ 2840-44-0 ]
7-fluoro-2-(4-pyridyl)hydroxymethyl-1-tetralone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol;	7-Fluoro-2-(4-pyridyl)hydroxymethyl-1-tetralone may be prepared in the following manner: 4-pyridinecarbaldehyde (59.2 g) is added to a mixture of <strong>[2840-44-0]7-fluoro-1-tetralone</strong> (45.4 g), methanol (140 cc) and 2N sodium hydroxide (41.5 cc) at a temperature of 5° C. The mixture is stirred at a temperature in the vicinity of 25° C. for 3 hours. The expected compound (68.8 g), m.p. 133° C., is isolated directly. 7-Fluoro-1-tetralone may be prepared according to the method described by G. A. THIAULT, Bull. Soc. Chim. France, 1308 (1965).

Reference： [1]Patent: US5114949,1992,A

4
[ 872-85-5 ]
[ 16619-14-0 ]
[ 1171953-00-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium hydroxide; In ethanol; water; at 20℃; for 24h;	An aqueous sodium hydroxide solution (6N, 2 mL) is added to a solution of 2- phenyl - 2, 3 - dihydroquinolin-4(lH)-one (223 mg, lmmol) in ethanol (5mL). Pyridine -4- carboxaldehyde (126 mg, 1.2 mmol) is then added to the reaction mixture, which is stirred at room temperature for 24 hours. Subsequently, it is evaporated under reduced pressure. The residue is dissolved into chloroform and the organic layer washed with water, dried over Na2SO4 and evaporated to dryness. Crude product further purified by column chromatography on silica gel using ethyl acetate: acetone (97:03 v/v) as eluent. Yield 130 mg (42percent); mp 222-224°C; IR (KBR) 3435, 1627 cm"1; 13C NMR (DMSO-d6) delta 30.84 (CH2), 116.04 (C-8), 118.40 (C-6), 123.16 (C-3), 123.39 (C-2" and C-6"), 123.76 (C-4'), 125.09 (C-4a), 128.61 (C-2' and C-6'), 128.66 (C-3' and C-5'), 129.67 (C-5), 131.73 (C-7), 134.58 (C-I'), 139.65 (C-2), 149.16 (C-3" and C-5"), 149.64 (C-I"), 150.49 (C-8a), 176.21 (C=O).

Reference： [1]Patent: WO2009/87684,2009,A2 .Location in patent: Page/Page column 29

5
[ 872-85-5 ]
[ 35661-51-9 ]
[ 1158960-30-5 ]

Reference： [1]Synthesis,2009,p. 1007 - 1013

6
[ 872-85-5 ]
[ 62327-21-3 ]
[ 190265-08-8 ]

Yield	Reaction Conditions	Operation in experiment
		20 g (89 mmol) of T-BUTYL-P, P-dimethylphosphonoacetate in 50 ml of THF is added in drops at 0°C to a suspension of 3.9 g (98 mmol) of sodium hydride (60 percent in mineral oil) in 250 ml of THF. After 1 hour of stirring at 0°C, a solution of 10 g (93 mmol) of pyridine-4- carbaldehyde in 50 ml of tetrahydrofuran is added in drops, and the reaction mixture is stirred for 1 hour at 0°C and for 18 hours at room temperature. The precipitated solid is removed by filtration, and the solution is concentrated by evaporation. The residue is dissolved in isopro- panol while being heated, non-soluble portions are filtered off, and the solution is cooled to 0°C for crystallization. The solid that is produced is filtered off, stirred with hexane, filtered and dried. The intermediate product (15.3 g) is hydrogenated in 150 ml of ethanol with 0.15 g of 10percent palladium/activated carbon for 6 hours. The catalyst is filtered off, the solution is concentrated by evaporation, and the residue is filtered on silica gel (mobile solvent diethyl ether). 13.0 g of a light yellow oil (71percent of theory) is obtained.

Reference： [1]Patent: WO2004/65491,2004,A1 .Location in patent: Page 18-19

7
[ 872-85-5 ]
[ 62327-21-3 ]
[ 501379-44-8 ]

Yield	Reaction Conditions	Operation in experiment
71%		20 g (89 mmol) of t-butyl-P,P-dimethylphosphonoacetate in 50 ml of THF is added in drops at O0C to a suspension of 3.9 g (98 mmol) of sodium hydride (60 percent in mineral oil) in 250 ml of THF. After 1 hour of stirring at 00C, a solution of 10 g (93 mmol) of pyridine-4- carbaldehyde in 50 ml of tetrahydrofuran is added in drops, and the reaction mixture is stirred for 1 hour at O0C and for 18 hours at room temperature. The precipitated solid is removed by filtration, and the solution is concentrated by evaporation. The residue is dissolved in isopropanol while being heated, non-soluble portions are filtered off, and the solution is cooled to 0°C for crystallization. The solid that is produced is filtered off, stirred with hexane, filtered and dried. The intermediate product (15.3 g) is hydrogenated in 150 ml of ethanol with 0.15 g of 10percent palladium/activated carbon for 6 hours. The catalyst is filtered off, the solution is concentrated by evaporation, and the residue is filtered on silica gel (mobile solvent diethyl ether). 13.0 g of a light yellow oil (71percent of theory) is obtained.

Reference： [1]Patent: WO2006/8179,2006,A2 .Location in patent: Page/Page column 29-30

8
[ 872-85-5 ]
[ 538-28-3 ]
[ 105-56-6 ]
2-(benzylthio)-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Research on Chemical Intermediates,2012,vol. 38,p. 983 - 993

9
[ 872-85-5 ]
[ 766-36-9 ]
(E)-3-ethyl-4-methyl-5-((pyridin-4-yl)methylene)-1H-pyrrol-2(5H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6292 - 6302

10
[ 872-85-5 ]
[ 766-36-9 ]
(Z)-3-ethyl-4-methyl-5-((pyridin-4-yl)methylene)-1H-pyrrol-2(5H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6292 - 6302

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Isomers

Technical Information

? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Pharmaceutical Intermediates of
[ 872-85-5 ]

Donepezil Related Intermediates

[ 120014-07-5 ]

2-((1-Benzylpiperidin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Related Functional Groups of
[ 872-85-5 ]

Aldehydes

[ 99163-12-9 ]

4-(Pyridin-4-yl)benzaldehyde

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[ 176526-00-4 ]

2-(Pyridin-4-yl)benzaldehyde

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[ 127406-55-7 ]

4-(Pyridin-3-yl)benzaldehyde

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[ 63875-01-4 ]

2-Methylisonicotinaldehyde

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[ 100910-66-5 ]

5-Methylnicotinaldehyde

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Related Parent Nucleus of
[ 872-85-5 ]

Pyridines

[ 99163-12-9 ]

4-(Pyridin-4-yl)benzaldehyde

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[ 176526-00-4 ]

2-(Pyridin-4-yl)benzaldehyde

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4-Acetylpyridine

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4-(Pyridin-3-yl)benzaldehyde

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2-Methylisonicotinaldehyde

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Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 872-85-5 ] {[proInfo.proName]}

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[ 872-85-5 ] Synthesis Path-Upstream 1~1

[ 872-85-5 ] Synthesis Path-Downstream 1~10

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Aldehydes

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Pyridines

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[ 872-85-5 ]

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