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[ CAS No. 51298-62-5 ] {[proInfo.proName]}

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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 51298-62-5
Chemical Structure| 51298-62-5
Structure of 51298-62-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51298-62-5 ]

CAS No. :51298-62-5 MDL No. :MFCD00039052
Formula : C7H16ClN5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :QBNXAGZYLSRPJK-JEDNCBNOSA-N
M.W : 269.69 Pubchem ID :135193
Synonyms :
NG-Nitroarginine methyl ester hydrochloride;L-NAME (hydrochloride);H-Arg(NO2)-OMe.HCl;51298-62-5;N(G)-Nitro-L-arginine methyl ester;L-NG-Nitroarginine methyl ester;N-Nitro-L-arginine methylester;NG-Nitroarginine methyl ester;L-NAME HCl

Calculated chemistry of [ 51298-62-5 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 9
Num. H-bond acceptors : 6.0
Num. H-bond donors : 4.0
Molar Refractivity : 64.02
TPSA : 146.05 Ų

Pharmacokinetics

GI absorption : Low
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) : -7.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.15
Log Po/w (WLOGP) : -0.63
Log Po/w (MLOGP) : -0.67
Log Po/w (SILICOS-IT) : -3.04
Consensus Log Po/w : -0.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.01
Solubility : 26.2 mg/ml ; 0.0972 mol/l
Class : Very soluble
Log S (Ali) : -2.77
Solubility : 0.454 mg/ml ; 0.00168 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.45
Solubility : 96.6 mg/ml ; 0.358 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 5.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.01

Safety of [ 51298-62-5 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P501-P261-P270-P240-P210-P241-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 UN#:1325
Hazard Statements:H302+H312+H332-H315-H319-H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 51298-62-5 ]

* 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.

  • Downstream synthetic route of [ 51298-62-5 ]

[ 51298-62-5 ] Synthesis Path-Downstream   1~29

  • 2
  • [ 3257-18-9 ]
  • [ 51298-62-5 ]
  • [ 98422-13-0 ]
  • 3
  • [ 2362-45-0 ]
  • [ 51298-62-5 ]
  • [ 96868-07-4 ]
YieldReaction ConditionsOperation in experiment
(i) Et3N, THF, DMF, CH2Cl2, (ii) /BRN= 1188572/, DCC; Multistep reaction;
  • 5
  • [ 5680-86-4 ]
  • [ 51298-62-5 ]
  • [ 106066-16-4 ]
  • 6
  • [ 3479-47-8 ]
  • [ 51298-62-5 ]
  • Cbo-L-Asp-(β-benzylester)-nitro-L-Arg-methylester [ No CAS ]
  • 7
  • [ 51298-62-5 ]
  • [ 10342-01-5 ]
  • BOC-Ser(CH2-C6H5)-Arg(NO2)-OCH3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide
  • 8
  • [ 51298-62-5 ]
  • [ 17350-17-3 ]
  • [ 6464-80-8 ]
YieldReaction ConditionsOperation in experiment
95% With N-Ethylmaleimide; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 18h; pH 7.0-7.5;
  • 9
  • [ 39608-31-6 ]
  • [ 51298-62-5 ]
  • Z-Sar-Arg(NO2)-OMe [ No CAS ]
  • 10
  • [ 51298-62-5 ]
  • [ 313952-15-7 ]
  • [ 373368-82-2 ]
YieldReaction ConditionsOperation in experiment
91% With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 22.5h;
90% With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 22.5h;
  • 11
  • [ 51298-62-5 ]
  • [ 313952-10-2 ]
  • [ 373369-17-6 ]
YieldReaction ConditionsOperation in experiment
46% With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 24.5h;
64 mg With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 22.5h;
  • 12
  • [ 51298-62-5 ]
  • [ 1784-05-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) triethylamine / dioxane / 1.) RT, 1 h, 2.) RT, 12 h 2: hydrogen, HCl / PdCl2 / methanol / Ambient temperature
  • 13
  • [ 32991-17-6 ]
  • [ 51298-62-5 ]
  • [ 1208130-71-5 ]
  • 15
  • [ 51298-62-5 ]
  • [ 15401-08-8 ]
  • C22H37N7O8 [ No CAS ]
  • 16
  • [ 51298-62-5 ]
  • [ 52071-65-5 ]
  • C26H39N7O8 [ No CAS ]
  • 17
  • [ 955095-30-4 ]
  • [ 51298-62-5 ]
  • [ 1426327-01-6 ]
YieldReaction ConditionsOperation in experiment
86% With sodium triacetoxyborohydride; acetic acid In N,N-dimethyl-formamide; toluene at 90℃; Molecular sieve;
  • 18
  • [ 160880-11-5 ]
  • [ 51298-62-5 ]
  • [ 1431978-35-6 ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-3-methoxybenzoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 19
  • [ CAS Unavailable ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: C12H14O3; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 20
  • [ 27780-18-3 ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: p-[(3,7-dimethyl-2,6-octadienyl)oxy]benzoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 21
  • [ CAS Unavailable ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: p-isopentenoxybenzenepropanoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 22
  • [ 1191456-98-0 ]
  • [ 51298-62-5 ]
  • [ 1431978-39-0 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 3-(4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}phenyl)propanoic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 23
  • [ 870073-93-1 ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 4'-Geranyloxyferulic acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 24
  • [ CAS Unavailable ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: C14H16O3; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 25
  • [ 183584-02-3 ]
  • [ 51298-62-5 ]
  • [ 1431978-33-4 ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: Geranyloxy-p-coumaric acid; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 26
  • [ CAS Unavailable ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: C13H16O4; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 27
  • [ CAS Unavailable ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: C15H18O4; nitro-L-arginine methyl ester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In dichloromethane at 20℃; for 24h; Coupling of benzoic or cinnamic acid derivatives with L-NAME. General procedure General procedure: To a stirred solution of the acid (1.0 mmol) in CH2Cl2 (30 mL) L-NAME (1.1 mmol) and triethylamine (1.2 mmol) were added. After 15 min a solution of EEDQ (1.0 mmol) in CH2Cl2 (15 mL) was added dropwise over a period of 10 min. Further EEDQ solution additions (1.0 mmol each) were made after 5 h and 10 h respectively. After 24 h the reaction mixture was washed in sequence with NaHCO3 (aq) 2% (2 x 30 mL) and citric acid 1% (2 x 30 mL). The organic phase is evaporated to dryness under vacuum and n-hexane (50 mL) was added to the resulting yellowish solid and the resulting suspension stirred for 30 min at r.t.. The white solid separated was then filtered and collected, providing the desired product in pure form.
  • 28
  • [ 2566-22-5 ]
  • [ 51298-62-5 ]
  • [ 1208130-69-1 ]
  • 29
  • [ 1309878-67-8 ]
  • [ 51298-62-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Stage #2: nitro-L-arginine methyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 36h; General procedure D for the synthesis of compound 9a. General procedure: To a stirred solution of the acid derivative 4b(100 mg, 0.241 mmol, 1.0 equiv) in anhydrous CH2Cl2 (4 mL) was added HOBT (72 mg, 0.530 mmol, 2.2equiv), EDC·HCl (103 mg, 0.530 mmol, 2.2 equiv). The solution was then stirred for 30 min at sametemperature. The resultant solution was then transferred to 0 °C and DIPEA (116 mg, 0.892 mmol, 3.0 equiv) was added dropwise to the solution followed by compound 8a (51 mg, 0.327 mmol, 1.1 equiv) andallowed to stirred for 36 h from 0 oC to rt. After completion of starting material, the reaction mixture wasquenched by adding 5 mL saturated aqueous NaHCO3 solution and the aqueous layer was extracted withCH2Cl2 (3 ×10 mL). The solution was then washed with brine, dried over Na2SO4 and concentrated underreduced pressure to afford the crude ester derivative of acid-amine coupling product. The crude amideproduct was directly subjected to ester hydrolysis using LiOH.H2O (2.0 equiv) in THF and H2O (0.5 mL)at room temperature for 4 h (TLC monitored). Then the volatile was evaporated under reduced pressure andH2O (2 mL) was added to the reaction mixture followed by 10% aqueous HCl was added with a maintainedPH = 2. Further, it was extracted with CH2Cl2 (2 ×10 mL). The solution was then washed with brine, driedover Na2SO4 and concentrated under reduced pressure to afford the crude acid derivative which was directlysubjected to column chromatography using 2-3% MeOH in DCM afforded the pure compound 9a in 84%yield as a white solid over two-steps.
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