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Quality Control of 4-Aminobenzoic acid Purity: 98% SDS Specification

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Product Citations

Development of Open Lactam and Captopril Analogues for the Covalent Inhibition of Metallo-β-Lactamases

Ohoueu, Marie-Josiane ;

Abstract: The synthesis of a series of compounds designed to act as inhibitors of metallo-βlactamase enzymes (MBLs), a sub-class of β-lactamases found in several clinically difficult to treat bacteria that are responsible for the widespread β-lactam antibiotic resistance, are described. The strategy involves the introduction of a functional group, such as an epoxide or thiirane, in the designed inhibitors capable of covalently binding the MBL targets and shutting them down irreversibly. This would prevent the enzymes from hydrolyzing the antibiotic drugs which would maintain their efficacy as a form of treatment. This was first attempted through the development of a convergent synthesis which involved the formation of L- and D-vinylglycine methyl ester, serving for the incorporation of the 3-membered ring, in a five-step synthetic pathway. This was subsequently introduced using coupling chemistry to a dipeptide. The intermediate dipeptide precursor synthesized through amino acid coupling was phenylglycine-serine (Phg-Ser) followed by a phenylacetic acid-serine (PAA-Ser), which both mimic an open lactam structure. They were subjected to halogenation to convert the serine alcohol functional group to a bromide for the alkylation reaction with the amino group contained in the protected vinylglycine. However, the bromination of Phg-Ser proved to be difficult while the formation of the desired tripeptide with the brominated PAA-Ser was not observed. Evidence of an alkene product was observed which was attributed to the acidic proton at the α-position favoring the elimination of the bromine. Those limitations led to the modification of the serine core to aspartic acid which was thought to circumvent the elimination issue by introducing the vinylglycine by amide bond formation rather than alkylation. Investigation with the phenylacetic-acid-aspartic acid dipeptide led to a promising route in which the coupling of the vinylglycine was achieved efficiently. The subsequent last steps of epoxidation of the alkene and deprotection seemed to be successful although optimization of these is still required. Another strategy for the development of covalent inhibitors was the synthesis of compounds inspired from L-captopril, an inhibitor of angiotensin converting enzyme (ACE) inhibitors which plays a role in heart attack. Here, the strategy involves the synthesis of an alkenecontaining intermediate with 2-methylprop-2-enoic acid or 2-methyl-3-butenoic acid through acylation of proline ethyl ester with the corresponding acyl chlorides. The intermediates were successfully obtained, enabling the formation of the epoxide and thiirane compounds. Subsequently, the ethyl ester hydrolysis was done to provide the final derivatives 1-(2-methyloxirane-2-carbonyl) pyrrolidine-2-carboxylic acid (82) and 1-(2-methylthiirane-2-carbonyl)pyrrolidine-2-carboxylic acid (83) with evidence of the formation of the desired 82 and 83. In the case of the longer chain analogues, 1-[2-(oxirane-2yl)propanoyl] pyrrolidine-2-carboylic acid (84) and 1-[2-(thiirane-2yl)propanoyl] pyrrolidine-2-carboylic acid (85), the deprotection led to the isolation of the final thiirane compound 85 in an overall 5% yield while this last deprotection step remains to be optimized to obtain 84. The synthetic pathway of the open lactam derivatives was overall successful with only the last two steps requiring further optimization which would provide a new class of β-lactamase inhibitors. The pathway for the development of the proline derivatives afforded efficiently one of the desired captopril derivatives while the purification of last step to isolate the remaining compounds needs to be improved. The strategy presented could be used in the future to provide further library compounds for MBL inhibition for further studies. General Introduction: This dissertation is composed of three separate chapters: (I) Introduction to β-lactamases and antimicrobial resistance, (II) Development of open lactam analogues as covalent inhibitors targeting metallo-β-lactamases, (III) Development of captopril-inspired compounds as covalent inhibitors of metallo-β-lactamases. The first chapter serves as introduction to the subject under the form of a mini review. The subsequent chapters investigate the strategies which have been explored in order to obtain the desired targets. They each are comprised of an introduction, results and discussion, and conclusion. Following the chapters is an appendix of relevant spectroscopic data related to the experimental procedures of the different chapters.

Purchased from AmBeed: 17527-29-6 ; 150-13-0 ; 53774-20-2 ; 138-39-6

Product Details of 4-Aminobenzoic acid

CAS No. :	150-13-0
Formula :	C₇H₇NO₂
M.W :	137.14
SMILES Code :	O=C(O)C1=CC=C(N)C=C1
Synonyms :	PABA; Vitamin Bx; Aminobenzoic acid
MDL No. :	MFCD00007894
InChI Key :	ALYNCZNDIQEVRV-UHFFFAOYSA-N
Pubchem ID :	978

Safety of 4-Aminobenzoic acid

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 4-Aminobenzoic acid

* 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 [ 150-13-0 ]
Downstream synthetic route of [ 150-13-0 ]

[ 150-13-0 ] Synthesis Path-Upstream 1~7

1
[ 150-13-0 ]
[ 22090-27-3 ]

References: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8524 - 8537,14.

2
[ 540-72-7 ]
[ 150-13-0 ]
[ 93-85-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With bromine In methanol at -10 - -5℃; for 2 h;	Synthesis of 2-aminobenzothiazole-6-carbolic Acid(2)NaSCN (65 g, 0.8 mol) was added to a suspension of commercially available 4-amino-benzoic acid (1, 100 g, 0.73 mol) in MeOH followed by the addition of Br₂(38 ml, 0.73 mol) in portions. The above solution was allowed to cool to -10° C. and stirred for 2 h while keeping the inner temperature below -5° C. The precipitate was then filtered and suspended in 350 ml of 1 M HCl. The suspension was heated to reflux for 30 min. After immediate filtration, 150 ml concd HCl was added to the hot filtrate to give 70 g (yield 42percent) of 2-amino-benzothiazole-6-carboxylic acid (2) (as a white solid), which was dried and used without further purification.

References: [1] Patent: US2009/123373, 2009, A1, . Location in patent: Page/Page column 14-15.

3
[ 333-20-0 ]
[ 150-13-0 ]
[ 93-85-6 ]

References: [1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222.
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 5, p. 494 - 498.
[3] Patent: WO2010/62171, 2010, A2, . Location in patent: Page/Page column 156.
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5561 - 5565.
[5] Patent: KR2018/81285, 2018, A, . Location in patent: Paragraph 0132; 0144-0147.

4
[ 150-13-0 ]
[ 93-85-6 ]

References: [1] Patent: US5710012, 1998, A, .

5
[ 150-13-0 ]
[ 93-85-6 ]

References: [1] Letters in Drug Design and Discovery, 2011, vol. 8, # 9, p. 717 - 724.
[2] Letters in Drug Design and Discovery, 2011, vol. 8, # 8, p. 717 - 724.

6
[ 1147550-11-5 ]
[ 150-13-0 ]
[ 93-85-6 ]

References: [1] Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 10,30.
[2] Arzneimittel Forschung, 1952, vol. 2, p. 455,460.

7
[ 15192-76-4 ]
[ 150-13-0 ]
[ 93-85-6 ]

References: [1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112.

[ 150-13-0 ] Synthesis Path-Downstream 1~30

1
[ 91-22-5 ]
[ 98-88-4 ]
[ 150-13-0 ]
[ 582-80-9 ]

References: [1]Chemische Berichte,1910,vol. 43,p. 2578.

2
[ 582-80-9 ]
[ 150-13-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1880,vol. 205,p. 118.

3
[ 98-88-4 ]
[ 150-13-0 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 582-80-9 ]

References: [1]Chemische Berichte,1910,vol. 43,p. 2578.

4
[ 98-88-4 ]
[ 150-13-0 ]
[ 582-80-9 ]

Yield	Reaction Conditions	Operation in experiment
96.7%		PREPARATION EXAMPLE EX45 (0284) This example demonstrates the production of 4-benzoylamino benzoic acid having the following structure (0285) (0286) In a 1 L beaker with mechanical stirring, 27.4 g of 4-aminobenzoic acid (0.2 mol) was mixed in 300 mL of DI H2O. Then, 21.2 g (0.2 mol) of sodium carbonate was added until the pH value became 9.1 and all the 4-amino benzoic acid dissolved in the water. (0287) Then, 56.24 g (0.4 mol) of benzoyl chloride was added dropwise to the beaker at room temp. The reaction was stirred overnight. A solid formed during the reaction, and the pH stabilized at 4.0. The pH was further lowered to about 2 with hydrochloric acid. The product was collected by filtration and washed with hot water to remove excess benzoic acid. The solid product was dried in an oven at 110° C. and 44.21 g of the product was obtained (yield 96.7percent).
81%	With pyridine; at 20℃;	General procedure: Aromatic halides (1.0 equivalent) were added dropwise to the stirred solution of aminobenzoic acids (200 mg) in pyridine. Mixtures were stirred at room temperature for about all target derivatives except of benzyl based derivative. The pH of reaction mixtures was kept basic using pyridine. Progress of the reaction was monitored using TLC plates. Upon complete formation of target compounds, the desired products were filtered as white precipitates. For benzyl based derivatives reaction mixture was refluxed for more than 24 hours and product was obtained by evaporating the solvent under vacuum.
		General procedure: A solution of aminobenzoic acid in dichloromethane at room temperature was treated with triethylamine and stirred for 30 min to obtain a pellucid solution. The substituted benzoyl chloride was then slowly added. After precipitates were observed, the mixture was stirred at room temperature for another 2 h. The suspension was concentrated under reduced pressure, and the residue was purified by hot acetic acid to give compounds 4a-f.

References: [1]Patent: US9200142,2015,B2 .Location in patent: Page/Page column 50.
[2]Acta poloniae pharmaceutica,2018,vol. 75,p. 385 - 396.
[3]Synthetic Communications,2008,vol. 38,p. 4068 - 4075.
[4]Chemische Berichte,1910,vol. 43,p. 2578.
[5]Journal of the American Chemical Society,1956,vol. 78,p. 2570.
[6]Bulletin de la Societe Chimique de France,1951,p. 220,222.
[7]Chemische Berichte,1910,vol. 43,p. 2578.
[8]Journal of Medicinal Chemistry,1988,vol. 31,p. 590 - 603.
[9]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 2139 - 2141.
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 2394 - 2396.
[10]Russian Journal of Physical Chemistry,1996,vol. 70,p. 2004 - 2006.
[11]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1739 - 1742.
[12]Journal of Organic Chemistry,2013,vol. 78,p. 11765 - 11771.

5
[ 28785-06-0 ]
[ 150-13-0 ]
[ 64518-50-9 ]

References: [1]Patent: DE2701854,1977, .
Chem.Abstr.,1977,vol. 87.

6
[ 2439-54-5 ]
[ 150-13-0 ]
[ 66974-67-2 ]

References: [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1052 - 1054.

7
[ 150-13-0 ]
2-benzoylthio-1-methylpyridinium chloride [ No CAS ]
[ 582-80-9 ]

References: [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 247 - 254.

8
[ 150-13-0 ]
[ 65-85-0 ]
[ 582-80-9 ]

References: [1]Journal of Chemical Research - Part S,1998,p. 268 - 269.

9
[ 2797-52-6 ]
[ 150-13-0 ]
[ 582-80-9 ]

References: [1]Journal of Chemical Research - Part S,2003,p. 121 - 123.

10
[ 150-13-0 ]
[ 848417-68-5 ]
[ 582-80-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2004,vol. 43,p. 927 - 935.

11
[ 5423-67-6 ]
[ 150-13-0 ]
6-[(4-carboxyphenyl)azo]-3-hydroxy-7,8-benzo-1,2,3,4-tetrahydroquinoline [ No CAS ]

References: [1]Russian Chemical Bulletin,2006,vol. 55,p. 1066 - 1070.

12
[ 150-13-0 ]
[ 3337-66-4 ]

References: [1]American Chemical Journal,1909,vol. 42,p. 457.

13
[ 628-36-4 ]
[ 150-13-0 ]
[ 122-51-0 ]
[ 624-84-0 ]
[ 157069-48-2 ]

References: [1]Dalton Transactions,2013,vol. 42,p. 7795 - 7802.

14
[ 6638-05-7 ]
[ 150-13-0 ]
C₂₅H₂₇NO₈ [ No CAS ]
C₂₁H₁₆N₂O₆ [ No CAS ]
[ 64518-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	With Galerina sp. HC1 laccase; oxygen; In aq. acetate buffer; at 22℃;pH 5.0;	General procedure: For the oxidation reactions 5mM of a model compound was allowed to react with 0.4U/mL laccase in 20mM sodium acetate buffer pH 5, at room temperature (?22°C) with mixing on rocking table (Mixer 440, Swelab Instrument AB, Sweden). The reaction was stopped by adding sodium azide to the final concentration of 40muM. The coupling of equimolar amount of PABA (5mM) to the compounds was also investigated under similar conditions.

References: [1]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 97,p. 45 - 53.

15
[ 75-75-2 ]
[ 4506-66-5 ]
[ 150-13-0 ]
4,4′-(1,5-dihydroimidazo[4,5-f]benzimidazole-2,6-diyl)dianiline tetramesylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tin(II) chloride dihdyrate; In para-xylene; for 8.25h;Dean-Stark; Reflux; Inert atmosphere;	The preparation of 4,4?-(1,5-dihydroimidazo[4,5-f]benzimidazole-2,6-diyl)dianiline tetramesylate was accomplished following the same general procedure described in Example 4.

References: [1]Patent: US2014/66629,2014,A1 .Location in patent: Paragraph 0089; 0090.

16
[ 628-36-4 ]
[ 150-13-0 ]
[ 157069-48-2 ]

References: [1]Chemical Communications,2014,vol. 50,p. 5333 - 5335.

17
[ 55589-47-4 ]
[RuCl₂(hexamethylbenzene)]2 [ No CAS ]
[ 150-13-0 ]
C₂₆H₃₀ClN₂O₂Ru⁽¹⁺⁾*Cl^(1-) [ No CAS ]