Home Amines 130370-60-4
130370-60-4,MFCD00866533
Catalog No.:AA000U9F

130370-60-4 | Butanediamide, N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)-

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1mg
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5mg
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10mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA000U9F
Chemical Name:
Butanediamide, N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)-
CAS Number:
130370-60-4
Molecular Formula:
C23H31N3O4S2
Molecular Weight:
477.6399
MDL Number:
MFCD00866533
SMILES:
CNC(=O)[C@@H](NC(=O)[C@@H]([C@@H](C(=O)NO)CSc1cccs1)CC(C)C)Cc1ccccc1
Properties
Properties
 
Form:
Solid  
MP:
236-238°  
Solubility:
DMSO: ≥15mg/mL  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
614  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
12  
XLogP3:
3.5  

Downstream Synthesis Route

[1]Bailey,Stuart;Bolognese,Brian;Buckle,DerekR.;Faller,Andrew;Jackson,Sally;Louis-Flamberg,Pearl;McCord,Mark;Mayer,RuthJ.;Marshall,LisaA.;Smith,DavidG.[BioorganicandMedicinalChemistryLetters,1998,vol.8,#1,p.29-34]

CASUnavailable 
  130370-60-4 

[1]Bailey,Stuart;Bolognese,Brian;Buckle,DerekR.;Faller,Andrew;Jackson,Sally;Louis-Flamberg,Pearl;McCord,Mark;Mayer,RuthJ.;Marshall,LisaA.;Smith,DavidG.[BioorganicandMedicinalChemistryLetters,1998,vol.8,#1,p.29-34]

[1]Bailey,Stuart;Bolognese,Brian;Buckle,DerekR.;Faller,Andrew;Jackson,Sally;Louis-Flamberg,Pearl;McCord,Mark;Mayer,RuthJ.;Marshall,LisaA.;Smith,DavidG.[BioorganicandMedicinalChemistryLetters,1998,vol.8,#1,p.29-34]

[1]Bailey,Stuart;Bolognese,Brian;Buckle,DerekR.;Faller,Andrew;Jackson,Sally;Louis-Flamberg,Pearl;McCord,Mark;Mayer,RuthJ.;Marshall,LisaA.;Smith,DavidG.[BioorganicandMedicinalChemistryLetters,1998,vol.8,#1,p.29-34]

[1]Bailey,Stuart;Bolognese,Brian;Buckle,DerekR.;Faller,Andrew;Jackson,Sally;Louis-Flamberg,Pearl;McCord,Mark;Mayer,RuthJ.;Marshall,LisaA.;Smith,DavidG.[BioorganicandMedicinalChemistryLetters,1998,vol.8,#1,p.29-34]

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Title: Matrix metalloproteinases, tissue inhibitors of MMPs and TACE in experimental cerebral malaria.

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Title: Role of epidermal growth factor receptor transactivation in alpha1B-adrenoceptor phosphorylation.

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Journal: Atherosclerosis 20020801

Title: Generation of C-terminally truncated amyloid-beta peptides is dependent on gamma-secretase activity.

Journal: Journal of neurochemistry 20020801

Title: Inhibition of apoptosis in rat mesangial cells by tissue inhibitor of metalloproteinase-1.

Journal: Kidney international 20020701

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Title: Synthetic matrix metalloproteinase inhibitors inhibit growth of established breast cancer osteolytic lesions and prolong survival in mice.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020601

Title: Stromelysin-1 activation correlates with invasiveness in squamous cell carcinoma.

Journal: The Journal of investigative dermatology 20020501

Title: Role of calmodulin in the modulation of the MAPK signalling pathway and the transactivation of epidermal growth factor receptor mediated by PKC.

Journal: FEBS letters 20020424

Title: Increments in cytokines and matrix metalloproteinases in skeletal muscle after injection of tissue-damaging toxins from the venom of the snake Bothrops asper.

Journal: Mediators of inflammation 20020401

Title: Ligand-induced shedding of discoidin domain receptor 1.

Journal: FEBS letters 20020313

Title: MMP inhibition modulates TNF-alpha transgenic mouse phenotype early in the development of heart failure.

Journal: American journal of physiology. Heart and circulatory physiology 20020301

Title: Involvement of matrix metalloproteinase in thrombolysis-associated hemorrhagic transformation after embolic focal ischemia in rats.

Journal: Stroke 20020301

Title: Regulation of galectin-9 expression and release in Jurkat T cell line cells.

Journal: Glycobiology 20020201

Title: Expression of collagenase-3 (MMP-13) enhances invasion of human fibrosarcoma HT-1080 cells.

Journal: International journal of cancer 20020120

Title: Matrix and serine protease expression during leukemic cell differentiation induced by aclacinomycin and all-trans-retinoic acid.

Journal: Biochemical pharmacology 20020115

Title: Prostate cancer in bone: importance of context for inhibition of matrix metalloproteinases.

Journal: Journal of the National Cancer Institute 20020102

Title: Matrix metalloproteinase activity, bone matrix turnover, and tumor cell proliferation in prostate cancer bone metastasis.

Journal: Journal of the National Cancer Institute 20020102

Title: Matrix metalloproteinase-9 promotes neutrophil migration and alveolar capillary leakage in pancreatitis-associated lung injury in the rat.

Journal: Gastroenterology 20020101

Title: Thermolysin activates equine lamellar hoof matrix metalloproteinases.

Journal: Journal of comparative pathology 20020101

Title: Hyperthermia exhibits anti-vascular activity in the s.c. BT4An rat glioma: lack of interaction with the angiogenesis inhibitor batimastat.

Journal: International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group 20020101

Title: The metalloprotease-directed shedding of BP 180 (collagen XVII) from human keratinocytes in culture is unaffected by ceramide and cell-matrix interaction.

Journal: European journal of dermatology : EJD 20020101

Title: Perioperative matrix metalloproteinase inhibition therapy does not impair wound or anastomotic healing.

Journal: Journal of gastrointestinal surgery : official journal of the Society for Surgery of the Alimentary Tract 20020101

Title: The matrix metalloproteinase inhibitor batimastat inhibits the lung colonisation of orthotopically implanted malignant pancreatic tumor cells in SCID mice.

Journal: Swiss surgery = Schweizer Chirurgie = Chirurgie suisse = Chirurgia svizzera 20020101

Title: Combining antiangiogenic agents with metronomic chemotherapy enhances efficacy against late-stage pancreatic islet carcinomas in mice.

Journal: Cold Spring Harbor symposia on quantitative biology 20020101

Title: Transactivation of the epidermal growth factor receptor is involved in 12-O-tetradecanoylphorbol-13-acetate-induced signal transduction.

Journal: The Journal of biological chemistry 20011214

Title: Potentiation of docetaxel antitumor activity by batimastat against mouse forestomach carcinoma.

Journal: Chinese medical sciences journal = Chung-kuo i hsueh k'o hsueh tsa chih 20011201

Title: Inhibition of matrix metalloproteinases blocks lethal hepatitis and apoptosis induced by tumor necrosis factor and allows safe antitumor therapy.

Journal: Nature medicine 20011101

Title: Substrate specificity determinants of human macrophage elastase (MMP-12) based on the 1.1 A crystal structure.

Journal: Journal of molecular biology 20010928

Title: Membrane-type matrix metalloproteinase-1 and -3 activity in primate smooth muscle cells.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20010901

Title: Adipocyte produces matrix metalloproteinases 2 and 9: involvement in adipose differentiation.

Journal: Diabetes 20010901

Title: Activation of procollagenases is a key control point in cartilage collagen degradation: interaction of serine and metalloproteinase pathways.

Journal: Arthritis and rheumatism 20010901

Title: Quantitation of cell migration in a rat carotid artery balloon injury model. Indications for a perivascular origin of the neointimal cells.

Journal: Cardiovascular drugs and therapy 20010901

Title: Modulation of airway remodeling-associated mediators by the antifibrotic compound, pirfenidone, and the matrix metalloproteinase inhibitor, batimastat, during acute lung injury in mice.

Journal: European journal of pharmacology 20010824

Title: Regulation of matrix metalloproteinase activity in ischemic tissue by interleukin-10: role in ischemia-induced angiogenesis.

Journal: Circulation research 20010803

Title: Increased stromal expression of murine urokinase plasminogen activator in a human breast cancer xenograft model following treatment with the matrix metalloprotease inhibitor, batimastat.

Journal: Breast cancer research and treatment 20010801

Title: Shear-stress and wall-stress regulation of vascular remodeling after balloon angioplasty: effect of matrix metalloproteinase inhibition.

Journal: Circulation 20010703

Title: Functional role of matrix metalloproteinases (MMPs) in mammary epithelial cell development.

Journal: Journal of cellular physiology 20010701

Title: [An experimental study of matrix metalloproteinase inhibitor BB-94 inhibits the invasion and metastasis of the human salivary adenoid cystic carcinoma in vitro and in vivo].

Journal: Zhonghua kou qiang yi xue za zhi = Zhonghua kouqiang yixue zazhi = Chinese journal of stomatology 20010701

Title: A point mutation in the juxtamembrane stalk of human angiotensin I-converting enzyme invokes the action of a distinct secretase.

Journal: The Journal of biological chemistry 20010615

Title: Trastuzumab (herceptin), a humanized anti-Her2 receptor monoclonal antibody, inhibits basal and activated Her2 ectodomain cleavage in breast cancer cells.

Journal: Cancer research 20010615

Title: Proteolysis of the urokinase-type plasminogen activator receptor by metalloproteinase-12: implication for angiogenesis in fibrin matrices.

Journal: Blood 20010515

Title: In vitro evidence for a bacterial pathogenesis of equine laminitis.

Journal: Veterinary microbiology 20010402

Title: uPA/plasmin system-mediated MMP-9 activation is implicated in bronchial epithelial cell migration.

Journal: Experimental cell research 20010401

Title: Inhibition of bleomycin-induced pulmonary fibrosis in mice by the matrix metalloproteinase inhibitor batimastat.

Journal: The Journal of pathology 20010401

Title: Validation of an orthotopic model of human lung cancer with regional and systemic metastases.

Journal: The Annals of thoracic surgery 20010401

Title: Epilysin, a novel human matrix metalloproteinase (MMP-28) expressed in testis and keratinocytes and in response to injury.

Journal: The Journal of biological chemistry 20010330

Title: A possible role for metalloproteinases in renal cyst development.

Journal: American journal of physiology. Renal physiology 20010301

Title: Hydroxamate-type matrix metalloproteinase inhibitor batimastat promotes liver metastasis.

Journal: Cancer research 20010215

Title: Development of matrix metalloproteinase inhibitors in cancer therapy.

Journal: Journal of the National Cancer Institute 20010207

Title: HIV-1 Tat neurotoxicity is prevented by matrix metalloproteinase inhibitors.

Journal: Annals of neurology 20010201

Title: Renal matrix metalloproteinase activity is unaffected by experimental ischemia-reperfusion injury and matrix metalloproteinase inhibition does not alter outcome of renal function.

Journal: Experimental nephrology 20010101

Title: A matrix metalloproteinase inhibitor, batimastat, retards the development of osteolytic bone metastases by MDA-MB-231 human breast cancer cells in Balb C nu/nu mice.

Journal: European journal of cancer (Oxford, England : 1990) 20010101

Title: Beneficial effects of Batimastat (BB-94), a matrix metalloproteinase inhibitor, in rat experimental colitis.

Journal: Digestion 20010101

Title: Matrix metalloproteinases in the progression of heart failure: potential therapeutic implications.

Journal: Drugs 20010101

Title: An ex vivo angiogenesis assay utilizing commercial porcine carotid artery: modification of the rat aortic ring assay.

Journal: Angiogenesis 20010101

Title: Tyrosine phosphorylation and proteolysis. Pervanadate-induced, metalloprotease-dependent cleavage of the ErbB-4 receptor and amphiregulin.

Journal: The Journal of biological chemistry 19980807

Title: Yin Z, et al. Increased MMPs expression and decreased contraction in the rat myometrium during pregnancy and in response to prolonged stretch and sex hormones. Am J Physiol Endocrinol Metab. 2012 Jul 1;303(1):E55-70.

Title: Botos I, et al. Batimastat, a potent matrix mealloproteinase inhibitor, exhibits an unexpected mode of binding. Proc Natl Acad Sci U S A. 1996 Apr 2;93(7):2749-54.

Title: Hansen HP, et al. Inhibition of metalloproteinases enhances the internalization of anti-CD30 antibody Ki-3 and the cytotoxic activity of Ki-3 immunotoxin. Int J Cancer. 2002 Mar 10;98(2):210-5.

Title: Giavazzi R, et al. Batimastat, a synthetic inhibitor of matrix metalloproteinases, potentiates the antitumor activity of cisplatin in ovarian carcinoma xenografts. Clin Cancer Res. 1998 Apr;4(4):985-92.

Title: Ricci S, et al. Inhibition of matrix metalloproteinases attenuates brain damage in experimental meningococcal meningitis. BMC Infect Dis. 2014 Dec 31;14:726.

Title: Russo LA, et al. Regulated expression of matrix metalloproteinases, inflammatory mediators, and endometrial matrix remodeling by 17beta-estradiol in the immature rat uterus. Reprod Biol Endocrinol. 2009 Nov 4;7:124.

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Tags:130370-60-4 Molecular Formula|130370-60-4 MDL|130370-60-4 SMILES|130370-60-4 Butanediamide, N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)-