[ CAS No. 122334-37-6 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 122334-37-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 122334-37-6 ]

SDS Specification

Alternatived Products of [ 122334-37-6 ]

Product Citations

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 [ 122334-37-6 ]

CAS No. :	122334-37-6	MDL No. :	MFCD02684308
Formula :	C₉H₁₀ClNO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	LHUOAIXJPPMULP-UHFFFAOYSA-N
M.W :	199.63	Pubchem ID :	11275663
Synonyms :

Calculated chemistry of [ 122334-37-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.43
TPSA :	29.54 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	1.97
Log Po/w (MLOGP) :	2.35
Log Po/w (SILICOS-IT) :	1.45
Consensus Log Po/w :	2.05

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.52
Solubility :	0.604 mg/ml ; 0.00303 mol/l
Class :	Soluble
Log S (Ali) :	-2.31
Solubility :	0.98 mg/ml ; 0.00491 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.82
Solubility :	0.304 mg/ml ; 0.00152 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Safety of [ 122334-37-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 122334-37-6 ]

* 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 [ 122334-37-6 ]
Downstream synthetic route of [ 122334-37-6 ]

[ 122334-37-6 ] Synthesis Path-Upstream 1~1

1
[ 21406-61-1 ]
[ 122334-37-6 ]
[ 7295-50-3 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 7, p. 1427 - 1429

[ 122334-37-6 ] Synthesis Path-Downstream 1~1

1
[ 24134-09-6 ]
[ 122334-37-6 ]
[ 235092-30-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a 50-mL round-bottom flask containing a solution of <strong>[24134-09-6]5-bromo-1,2-dimethyl-1H-imidazole</strong> (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

Reference： [1]Patent: US2014/107097,2014,A1 .Location in patent: Paragraph 0334; 0335

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Isomers

Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

Historical Records

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[ 122334-37-6 ]

Aryls

[ 145959-21-3 ]

3-Chloro-N-methoxy-N-methylbenzamide

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[ 122334-36-5 ]

N-Methoxy-N,4-dimethylbenzamide

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N-Methoxy-N-methylbenzamide

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3-Chloro-N-methoxy-N-methylbenzamide

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Code	Phrase
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
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P402 + P404	Store in a dry place. Store in a closed container.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
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H200	Unstable explosive
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[ CAS No. 122334-37-6 ] {[proInfo.proName]}

Quality Control of [ 122334-37-6 ]

Related Doc. of [ 122334-37-6 ]

Product Citations

Product Details of [ 122334-37-6 ]

Calculated chemistry of [ 122334-37-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 122334-37-6 ]

Application In Synthesis of [ 122334-37-6 ]

[ 122334-37-6 ] Synthesis Path-Upstream 1~1

[ 122334-37-6 ] Synthesis Path-Downstream 1~1

Technical Information

Related Functional Groups of [ 122334-37-6 ]

Aryls

Chlorides

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 122334-37-6 ]