[ CAS No. 56-41-7 ] {[proInfo.proName]}

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Quality Control of [ 56-41-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 56-41-7 ]

SDS Specification

Alternatived Products of [ 56-41-7 ]

Product Citations Expand+

Rebamipide and Derivatives are Potent, Selective Inhibitors of Histidine Phosphatase Activity of the Suppressor of T Cell Receptor Signaling Proteins

Faisal Aziz ; Kanamata Reddy ; Virneliz Fernandez Vega , et al. JMC,2024,67(3):1949-1960. DOI: 10.1021/acs.jmedchem.3c01763

Abstract: The suppressor of T cell receptor

Purchased rebamipide, as a putative inhibitor of Sts phosphatase activity. Rebamipide, and a small library of derivatives, are competitive, selective inhibitors of Sts-1 with IC50 values from low to submicromolar. SAR analysis indicates that the quinolinone, the acid, and the amide moieties are all essential for activity. A crystal structure confirmed the SAR and reveals key interactions between this class of compound and the protein. Although rebamipide has poor cell permeability, we demonstrated that a liposomal preparation can inactivate the phosphatase activity of Sts-1 in cells. These studies demonstrate that Sts-1 enzyme activity can be pharmacologically inactivated and provide foundational tools and insights for the development of immune-enhancing therapies that target the Sts proteins.

from AmBeed: class="">2251-65-2 ; class="">90098-04-7 ; class="">4876-14-6 ; class="">90098-08-1 ; class="">874-60-2 ; class="">4876-10-2 ; class="">7158-32-9 ; class="">5271-67-0 ; class="">118-45-6 ; class="">73-22-3 ; class="">56-41-7 ; class="">34893-92-0 ; class="">403-43-0 ; class="">58757-38-3 ; class="">76903-88-3 ; class="span_more span_less">52-90-4 ; class="span_more span_less">6068-72-0 ; class="span_more span_less">2243-83-6 ; class="span_more span_less">38818-50-7 ; class="span_more span_less">16331-45-6 ; class="span_more span_less">36823-88-8 ; class="span_more span_less">90098-06-9 ; class="span_more span_less">90098-05-8 ; class="span_more span_less">3024-72-4 ; class="span_more span_less">618-46-2 ; class="span_more span_less">63024-43-1 ; class="span_more span_less">4122-68-3 ; class="span_more span_less">22980-09-2 ; class="span_more span_less">681806-75-7 ; class="span_more span_less">39544-74-6 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Antimycobacterial Rufomycin Analogues from Streptomyces atratus Strain MJM3502

Zhou, Bin ; Shetye, Gauri ; Yu, Yang , et al. J. Nat. Prod.,2020,83(3):657-667. DOI: 10.1021/acs.jnatprod.9b01095 PubMed ID: 32031795

Abstract: This study represents a systematic chem. and biol. study of the rufomycin (RUF) class of cyclic heptapeptides, which our anti-TB drug discovery efforts have identified as potentially promising anti-TB agents that newly target the caseinolytic protein C1, ClpC1. Eight new RUF analogs, rufomycins NBZ1-NBZ8, as well as 5 known peptides were isolated and characterized from the Streptomyces atratus strain MJM3502. Advanced Marfey's and X-ray crystallog. anal. led to the assignment of the absolute configuration of the RUFs. Several isolates exhibited potent activity against both pathogens M. tuberculosis H37Rv and M. abscessus, paired with favorable selectivity (selectivity index >60), which collectively underscores the promise of the rufomycins as potential anti-TB drug leads.

Purchased from AmBeed: 61-90-5 ; 3060-46-6 ; 56-41-7 ; 621-44-3

Product Details of [ 56-41-7 ]

CAS No. :	56-41-7	MDL No. :	MFCD00064410
Formula :	C₃H₇NO₂	Boiling Point :	-
Linear Structure Formula :	CH₃(NH₂)CHCOOH	InChI Key :	QNAYBMKLOCPYGJ-REOHCLBHSA-N
M.W :	89.09	Pubchem ID :	5950
Synonyms :	Alanine;2-Aminopropanoic Acid;NSC 206315;(2S)-2-Azaniumylpropanoate;(S)-Alanine;L-(+)-Alanine;α-Alanine

Calculated chemistry of [ 56-41-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	21.01
TPSA :	63.32 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.34
Log Po/w (XLOGP3) :	-2.96
Log Po/w (WLOGP) :	-0.58
Log Po/w (MLOGP) :	-3.06
Log Po/w (SILICOS-IT) :	-1.04
Consensus Log Po/w :	-1.46

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.54
Solubility :	3080.0 mg/ml ; 34.5 mol/l
Class :	Highly soluble
Log S (Ali) :	2.19
Solubility :	13800.0 mg/ml ; 155.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.77
Solubility :	523.0 mg/ml ; 5.87 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 56-41-7 ]

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 [ 56-41-7 ]

* 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.

Upstream synthesis route of [ 56-41-7 ]
Downstream synthetic route of [ 56-41-7 ]

[ 56-41-7 ] Synthesis Path-Upstream 1~7

1
[ 100-48-1 ]
[ 56-41-7 ]
[ 37398-49-5 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 15, p. 3738 - 3741

2
[ 87-72-9 ]
[ 56-41-7 ]
[ 3658-77-3 ]
[ 27538-10-9 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 1996, vol. 44, # 2, p. 531 - 536

3
[ 58-86-6 ]
[ 56-41-7 ]
[ 3658-77-3 ]
[ 27538-10-9 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 9, p. 2708 - 2713

4
[ 87-72-9 ]
[ 56-41-7 ]
[ 27538-10-9 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 1996, vol. 44, # 2, p. 531 - 536

5
[ 56-41-7 ]
[ 910902-20-4 ]
[ 2817-13-2 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1965, vol. 682, p. 244 - 249

6
[ 56-41-7 ]
[ 102156-97-8 ]
[ 2817-13-2 ]

Reference： [1] Chemische Berichte, 1960, vol. 93, p. 2983 - 3005

7
[ 7797-39-9 ]
[ 56-41-7 ]
[ 2817-13-2 ]

Reference： [1] Chemische Berichte, 1966, vol. 99, p. 2944 - 2954

[ 56-41-7 ] Synthesis Path-Downstream 1~11

1
[ 56-41-7 ]
[ 100-52-7 ]
[ 6940-80-3 ]

Reference： [1]Liebigs Annalen der Chemie,1994,p. 121 - 128

2
[ 56-41-7 ]
[ 72-18-4 ]
[ 2418-95-3 ]
[ 2799-07-7 ]
Ala-Asp-Cys-Phe-Trp-resin [ No CAS ]
2-[10-(4-amino-butyl)-19-[2-(2-amino-propionylamino)-3-carboxy-propionylamino]-16-benzyl-13-(1<i>H</i>-indol-3-ylmethyl)-7-methyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloeicosane-4-carbonyl]-amino}-3-methyl-butyric acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2002,vol. 41,p. 2940 - 2944

3
[ 56-41-7 ]
[ 72-18-4 ]
[ 2799-07-7 ]
[ 4727-00-8 ]
Ala-Asp-Cys-Phe-Trp-resin [ No CAS ]
2-[19-[2-(2-amino-propionylamino)-3-carboxy-propionylamino]-16-benzyl-7-(4-hydroxy-benzyl)-13-(1<i>H</i>-indol-3-ylmethyl)-10-methyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloeicosane-4-carbonyl]-amino}-3-methyl-butyric acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2002,vol. 41,p. 2940 - 2944

4
[ 56-41-7 ]
[ 72040-64-3 ]
(S)-2-{6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 927 - 933

5
[ 22280-60-0 ]
[ 56-41-7 ]
(S)-2-(6-methyl-5-nitro-pyridin-2-ylamino)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		Example 14 (S)-2-(6-Methyl-5-nitro-2-pyridin-2-ylamino)-propionic acid 6-Chloro-3-nitro-2-picoline (62 mg, 0.36 mmol) was coupled with Lralanine (80 mg, 0.90 mmol) and sodium acetate (78 mg, 0.95 mmol) in DMSO 1 mL. The reaction was heated to 140 C for 600 seconds in a microwave oven (Parameters: high absorbance, fixed holding time, pre-stirring 25 seconds). The crude mixture was treated with a saturated aqueous solution of N, C1. The reaction mixture was acidified to pH 4 (HCl, 1M). The crude reaction mixture was extracted with EtOAc, and the combined organic layers were washed with water and brine. Purification on silica using a mobile phase CH2Cl2-MeOH-HOAc gave 60 mg (74%) of (S)-2-(6-methyl-5-nkro-2-pyridin-2- ylamino)-propionic acid as a yellow solid.

Reference： [1]Patent: WO2005/42464,2005,A1 .Location in patent: Page/Page column 37

6
[ 56-41-7 ]
[ 56-87-1 ]
[ 131543-46-9 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 2470 - 2478

7
[ 56-41-7 ]
[ 56-87-1 ]
[ 131543-46-9 ]
[ 290-37-9 ]
[ 13925-00-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 4697 - 4708

8
[ 56-41-7 ]
[ 2401-21-0 ]
[ 1434517-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h;Inert atmosphere;	Synthesis of 17: A mixture of L-alanine (163 mg, 1.82 mmol), CS2CO3 (1.19 g, 3.65 mmol), and Cul (69.7 mg, 0.36 mmol) was added to the stirred solution of 1,2-dichloro-3- iodobenzene or 1,2-difluoro-3-iodobenzene (1.83 mmol) in dry DMF (3 mL) under a nitrogen atmosphere. The reaction mixture was heated at 90 C for 24 h. After completion, the reaction mixture was allowed to cool and water was added. The pH was adjusted to 3-5 by the addition of 2 N HC1 and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgS04, filtered and concentrated under reduced pressure. The crude acid 16 was used in the next step without further purification

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4028 - 4043
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 4739 - 4756
[3]Patent: WO2019/210160,2019,A1 .Location in patent: Page/Page column 52-53

9
[ 1454-85-9 ]
[ 56-41-7 ]
C₂₀H₄₁NO₂*ClH [ No CAS ]

Reference： [1]Langmuir,2015,vol. 31,p. 9546 - 9556

10
[ 1454-85-9 ]
[ 56-41-7 ]
C₂₀H₄₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene; at 110℃;	General procedure: L-alanine esters were preparedaccording to a procedure reported earlier.5,6 Lalanine(1.0 mmol), 1-alcohol (1.0 mmol) and ptoluenesulphonicacid monohydrate (1.2 mmol) weretaken in about 30 mL of toluene and refluxed at 110C.After 5-6 h of refluxing, the solvent was removedby rotary evaporation under reduced pressure. Theresidue was dissolved in chloroform and washed with 10percent sodium carbonate and then dried with anhydrous Na2SO4.

Reference： [1]Journal of Chemical Sciences,2015,vol. 127,p. 1627 - 1635

11
[ 56-41-7 ]
[ 437-86-5 ]
C₁₀H₁₂N₂O₄ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 1273 - 1280

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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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