140646-99-7

Basic information

• Product Name: L-Proline, 1-[5-methoxy-2-nitro-4-(phenylmethoxy)benzoyl]-, methyl ester
• CAS NO: 140646-99-7
• Molecular Formula: C21H22N2O7
• Molecular Weight: 414.415
• Mol File: 140646-99-7.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-[5-methoxy-2-nitro-4-(phenylmethoxy)benzoyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-[5-methoxy-2-nitro-4-(phenylmethoxy)benzoyl]-, methyl ester(140646-99-7)
• EPA Substance Registry System: L-Proline, 1-[5-methoxy-2-nitro-4-(phenylmethoxy)benzoyl]-, methyl ester(140646-99-7)

Safety Data

• Hazardous Substances Data: 140646-99-7(Hazardous Substances Data)

Upstream product

• 60547-92-4 4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 64154-78-5 4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 1486-53-9 4-(benzyloxy)-3-methoxybenzoic acid 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 56441-97-5 methyl 4-(benzyloxy)-3-methoxybenzoate 
• 61032-41-5 methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate 
• 67-56-1 methanol 
• 64154-79-6 (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylic acid 

Downstream Products

• 166117-57-3 N-<2-Azido-4-(benzyloxy)-5-methoxybenzoyl>-L-proline methyl ester 
• 123355-42-0 8-Hydroxy-7-methoxy-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 140647-00-3 (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde dimethyl acetal 
• 140850-28-8 (2S)-N-(2-amino-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carboxaldehyde dimethyl acetal 
• 81307-24-6 (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 
• 132622-12-9 (11aS)-8-(benzyloxy)-1,2,3,10,11,11a-hexahydro-7-methoxy-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5,11-dione 
• 849795-72-8 (11aS)-8-benzyloxy-7-methoxy-1,2,3,9,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 
• 166117-58-4 1-[2-azido-4-(benzyloxy)-5-methoxybenzoyl]prolinal 
• 194783-42-1 (S)-8-Benzyloxy-7,11-dimethoxy-1,2,3,10,11,11a-hexahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 127810-79-1 8-benzyl DC-81 
• 482378-30-3 2-(10-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-decyl)-benzo[de]isoquinoline-1,3-dione 
• 482378-35-8 2-(10-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-decyl)-benzo[de]isoquinoline-1,3-dione 
• 482378-29-0 2-(8-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-octyl)-benzo[de]isoquinoline-1,3-dione 
• 482378-34-7 2-(8-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-octyl)-benzo[de]isoquinoline-1,3-dione 

Relevant articles and documents

Macrocyclic pyrrolobenzodiazepine dimers as antibody-drug conjugate payloads

Macrocyclic pyrrolobenzodiazepine dimers were designed and evaluated for use as antibody-drug conjugate payloads. Initial structure–activity exploration established that macrocyclization could increase the potency of PBD dimers compared with non-macrocyclic analogs. Further optimization overcame activity-limiting solubility issues, leading to compounds with highly potent (picomolar) activity against several cancer cell lines. High levels of in vitro potency and specificity were demonstrated with an anti-mesothelin conjugate.

NOVEL CYTOTOXIC AGENTS FOR CONJUGATION OF DRUGS TO CELL BINDING MOLECULE

Provided are cytotoxic agents, pyrrolo[2,1-c][1,4]benzodiazepine (PBD) derivatives, their conjugates with a cell-binding agent, the preparation and the therapeutic uses in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.

Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates

A novel series of methyl ester-terminated CS-linked pyrrolobenzodiazepine (PBD)-poly(N-methylpyrrole) conjugates (50a-f) has been synthesized and their DNA interaction evaluated by thermal denaturation, DNA footprinting, and in vitro transcription stop assays. The synergistic effect of attaching a PBD unit to a polypyrrole fragment is illustrated by the large increase in DNA binding affinity (up to 50-fold) compared to the individual PBD and pyrrole components. 50a-f were found to bind mainly to identical DNA sequences but with apparent binding site widths increasing with molecular length and the majority of sites conforming to the consensus motif 5′-XGXWz (z = 3 ± 1; W = A or T; X = any base but preferably a purine). They also provided robust sequence-selective blockade of transcription at sites corresponding approximately to their DNA footprints. 50a-f were shown to have good cellular/nuclear penetration properties, and a degree of correlation between cytotoxicity and DNA-binding affinity was observed.