Home Imidazoles 53910-25-1
53910-25-1,MFCD00078802
Catalog No.:AA0038LE

53910-25-1 | (8R)-3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol

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1mg
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5mg
in stock  
$120.00   $84.00
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10mg
≥98%
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$159.00   $111.00
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25mg
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$323.00   $226.00
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50mg
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100mg
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0038LE
Chemical Name:
(8R)-3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
CAS Number:
53910-25-1
Molecular Formula:
C11H16N4O4
Molecular Weight:
268.2691
MDL Number:
MFCD00078802
SMILES:
OC[C@H]1O[C@@H](C[C@@H]1O)n1cnc2c1NC=NC[C@H]2O
Properties
Computed Properties
 
Complexity:
356  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-2.1  

Upstream Synthesis Route

[1]Patent:TW2017/6283,2017,A,.Locationinpatent:Page/Pagecolumn7;8

[1]Patent:WO2005/27838,2005,A2,.Locationinpatent:Page/Pagecolumn26-27

[1]Patent:US5387725,1995,A,

[2]Patent:US5387725,1995,A,

Downstream Synthesis Route

[1]Patent:WO2005/27838,2005,A2

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Title: Extracorporeal photopheresis in addition to pentostatin in conditioning for canine hematopoietic cell transplantation: role in engraftment.

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Journal: Acta haematologica 20100101

Title: Pentostatin as rescue therapy for glucocorticoid-refractory acute and chronic graft-versus-host disease.

Journal: Annals of transplantation 20100101

Title: Skin response using NIH consensus criteria vs Hopkins scale in a phase II study for steroid-refractory chronic GVHD.

Journal: Bone marrow transplantation 20091201

Title: Paraneoplastic pemphigus associated with systemic mastocytosis.

Journal: American journal of hematology 20091201

Title: A genomic approach to improve prognosis and predict therapeutic response in chronic lymphocytic leukemia.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20091115

Title: Evaluation of pentostatin in corticosteroid-refractory chronic graft-versus-host disease in children: a Pediatric Blood and Marrow Transplant Consortium study.

Journal: Blood 20091112

Title: Phase II study of alemtuzumab in combination with pentostatin in patients with T-cell neoplasms.

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Journal: British journal of haematology 20090901

Title: Etanercept, mycophenolate, denileukin, or pentostatin plus corticosteroids for acute graft-versus-host disease: a randomized phase 2 trial from the Blood and Marrow Transplant Clinical Trials Network.

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Title: Long-term follow-up of 233 patients with hairy cell leukaemia, treated initially with pentostatin or cladribine, at a median of 16 years from diagnosis.

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Title: Has success spoiled hairy cell leukemia research? Key questions go unanswered, despite big gains.

Journal: Journal of the National Cancer Institute 20090318

Title: Mcl-1 expression predicts progression-free survival in chronic lymphocytic leukemia patients treated with pentostatin, cyclophosphamide, and rituximab.

Journal: Blood 20090115

Title: Thoracic subcutaneous infiltration: an unusual presentation of subcutaneous panniculitis-like T-cell lymphoma.

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Title: Cost-effectiveness of pentostatin compared with cladribine in the management of hairy cell leukemia in the United Kingdom.

Journal: Clinical therapeutics 20090101

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Title: Complete response in a patient with adult T-cell leukemia (ATL) treated with combination of alemtuzumab and pentostatin.

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Title: Adenosine deaminase 2 from chicken liver: purification, characterization, and N-terminal amino acid sequence.

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Journal: Leukemia & lymphoma 20040201

Title: [Levetiracetam hepatitis].

Journal: Medicina clinica 20040117

Title: Phase II study of pentostatin in advanced T-cell lymphoid malignancies: update of an M.D. Anderson Cancer Center series.

Journal: Cancer 20040115

Title: CD26 expression correlates with a reduced sensitivity to 2'-deoxycoformycin-induced growth inhibition and apoptosis in T-cell leukemia/lymphomas.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040115

Title: Pentostatin, chlorambucil and prednisone therapy for B-chronic lymphocytic leukemia: a phase I/II study by the Eastern Cooperative Oncology Group study E1488.

Journal: Leukemia & lymphoma 20040101

Title: Treatment of resistant/relapsing chronic lymphocytic leukemia with a combination regimen containing deoxycoformycin and rituximab.

Journal: Acta haematologica 20040101

Title: Conjunctival involvement with T-cell prolymphocytic leukemia: report of a case and review of the literature.

Journal: Survey of ophthalmology 20040101

Title: Purine analogs in leukemia.

Journal: Advances in pharmacology (San Diego, Calif.) 20040101

Title: Results of a phase II multicenter trial of pentostatin and rituximab in patients with low grade B-cell non-Hodgkin's lymphoma: an effective and minimally toxic regimen.

Journal: Clinical lymphoma 20031201

Title: Adenosine deaminase, a key enzyme in DNA precursors control, is a new p73 target.

Journal: Oncogene 20031127

Title: Granulomatous slack skin disease--disease features and response to pentostatin.

Journal: British journal of haematology 20031001

Title: Lymphodepleting effects and safety of pentostatin for nonmyeloablative allogeneic stem-cell transplantation.

Journal: Transplantation 20030915

Title: 2-deoxycoformycin in the treatment of T-large granular lymphocyte leukemia.

Journal: Leukemia research 20030901

Title: T-cell prolymphocytic leukemia with autoimmune manifestations in Nijmegen breakage syndrome.

Journal: Annals of hematology 20030801

Title: Pentostatin for the treatment of chronic graft-versus-host disease in children.

Journal: Journal of pediatric hematology/oncology 20030701

Title: Mechanism of action of purine analogues in chronic lymphocytic leukaemia.

Journal: British journal of haematology 20030601

Title: Successful treatment of a patient with hairy cell leukemia and pentostatin-induced autoimmune thrombocytopenia with rituximab.

Journal: American journal of hematology 20030501

Title: Therapeutic potential for transient inhibition of adenosine deaminase in systemic inflammatory response syndrome.

Journal: Critical care medicine 20030501

Title: Pentostatin and cyclophosphamide: an effective new regimen in previously treated patients with chronic lymphocytic leukemia.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030401

Title: Structure-based de novo design of non-nucleoside adenosine deaminase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20030324

Title: CD26: a novel treatment target for T-cell lymphoid malignancies? (Review).

Journal: International journal of oncology 20030301

Title: Extended follow-up of patients with hairy cell leukemia after treatment with cladribine.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030301

Title: Pentostatin in the treatment of hairy-cell leukemia.

Journal: Best practice & research. Clinical haematology 20030301

Title: Cladribine in the treatment of hairy-cell leukaemia.

Journal: Best practice & research. Clinical haematology 20030301

Title: Purine nucleoside analogues in the treatment of myleoid leukemias.

Journal: Leukemia & lymphoma 20030301

Title: Advances in the treatment of hairy-cell leukaemia.

Journal: The Lancet. Oncology 20030201

Title: T-cell prolymphocytic leukemia: update and focus on alemtuzumab (Campath-1H).

Journal: Hematology (Amsterdam, Netherlands) 20030201

Title: Deoxycoformycin-containing combination chemotherapy for adult T-cell leukemia-lymphoma: Japan Clinical Oncology Group Study (JCOG9109).

Journal: International journal of hematology 20030201

Title: Enantiospecific synthesis of carbapentostatins.

Journal: The Journal of organic chemistry 20030110

Title: Long-term outcome with pentostatin treatment in hairy cell leukemia patients. A French retrospective study of 238 patients.

Journal: Leukemia 20030101

Title: Pentostatin in T-non-Hodgkin's lymphomas: efficacy and effect on CD26+ T lymphocytes.

Journal: Oncology reports 20030101

Title: Extracorporeal photopheresis in the treatment of graft-vs-host disease.

Journal: Journal of cutaneous medicine and surgery 20030101

Title: 2'-Deoxyadenosine causes apoptotic cell death in a human colon carcinoma cell line.

Journal: Journal of biochemical and molecular toxicology 20030101

Title: Intraclonal diversity in a Sezary syndrome with a differential response to 2-deoxycoformycin of the two lymphoma cell populations.

Journal: British journal of haematology 20021201

Title: Rituximab: a useful drug for a repeatedly relapsed hairy cell leukemia patient.

Journal: Annals of hematology 20021201

Title: Simultaneous diagnosis of hairy cell leukemia and chronic lymphocytic leukemia/small lymphocytic lymphoma: a frequent association?

Journal: Leukemia 20020801

Title: Plasma and cellular pharmacology of 8-chloro-adenosine in mice and rats.

Journal: Cancer chemotherapy and pharmacology 20020801

Title: Pentostatin pharmacokinetics and dosing recommendations in patients with mild renal impairment.

Journal: Cancer chemotherapy and pharmacology 20020801

Title: Successful treatment of aplastic variant of hairy-cell leukaemia with deoxycoformycin.

Journal: Hematology (Amsterdam, Netherlands) 20020801

Title: Adenosine deaminase inhibition attenuates microvascular dysfunction and improves survival in sepsis.

Journal: American journal of respiratory and critical care medicine 20020701

Title: Eradication of virus-infected T-cells in a case of adult T-cell leukemia/lymphoma by nonmyeloablative peripheral blood stem cell transplantation with conditioning consisting of low-dose total body irradiation and pentostatin.

Journal: International journal of hematology 20020701

Title: [Successful treatment of hairy cell leukemia prolymphocytic variant with 2'-deoxycoformycin].

Journal: [Rinsho ketsueki] The Japanese journal of clinical hematology 20020701

Title: Hepatosplenic gammadelta T-cell lymphoma: complete response induced by treatment with pentostatin.

Journal: British journal of haematology 20020601

Title: Cd8(+)/V beta 5.1(+) large granular lymphocyte leukemia associated with autoimmune cytopenias, rheumatoid arthritis and vascular mammary skin lesions: successful response to 2-deoxycoformycin.

Journal: Hematological oncology 20020601

Title: Myelodysplasia terminating in acute myeloid leukemia in a hairy cell leukemia patient treated with 2-deoxycoformycin.

Journal: Leukemia & lymphoma 20020601

Title: Inhibiting adenosine deaminase modulates the systemic inflammatory response syndrome in endotoxemia and sepsis.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20020501

Title: A potential role for AMP-activated protein kinase in meiotic induction in mouse oocytes.

Journal: Developmental biology 20020501

Title: Epithelioid microgranulomas after Pentostatin therapy in hairy cell leukaemia.

Journal: Histopathology 20020501

Title: High-level expression of human thyroid-stimulating hormone in Chinese hamster ovary cells by co-transfection of dicistronic expression vectors followed by a dual-marker amplification strategy.

Journal: Biotechnology and applied biochemistry 20020201

Title: Immunosuppression with limited toxicity: the characteristics of nucleoside analogs and anti-lymphocyte antibodies used in non-myeloablative hematopoietic cell transplantation.

Journal: Cancer treatment and research 20020101

Title: Treatment of Langerhans cell histiocytosis with 2'-deoxycoformycin (2'-DCF).

Journal: The hematology journal : the official journal of the European Haematology Association 20020101

Title: Pentostatin effective as preparative regimen for kidney transplants.

Journal: Expert review of anticancer therapy 20011201

Title: A unique ring-expanded acyclic nucleoside analogue that inhibits both adenosine deaminase (ADA) and guanine deaminase (GDA; guanase): synthesis and enzyme inhibition studies of 4,6-diamino-8H-1-hydroxyethoxymethyl-8-iminoimidazo[4,5-e][1,3]diazepine.

Journal: Bioorganic & medicinal chemistry letters 20011119

Title: Successful treatment with low-dose splenic irradiation for massive splenomegaly in an elderly patient with hairy-cell leukemia.

Journal: European journal of haematology 20011001

Title: Puromycin aminonucleoside induces apoptosis and increases HNE in cultured glomerular epithelial cells(1).

Journal: Free radical biology & medicine 20010901

Title: Therapy of T cell lymphomas with pentostatin.

Journal: Annals of the New York Academy of Sciences 20010901

Title: 2'-Deoxycoformycin for hepatosplenic gammadelta T-cell lymphoma.

Journal: Leukemia & lymphoma 20010801

Title: Infectious complications of purine analog therapy.

Journal: Current opinion in infectious diseases 20010801

Title: Hepatosplenic T-cell lymphoma.

Journal: British journal of haematology 20010701

Title: [Successful treatment of hairy cell leukemia with pentostatin].

Journal: [Rinsho ketsueki] The Japanese journal of clinical hematology 20010701

Title: Nucleoside analogues in the treatment of haematological malignancies.

Journal: Expert opinion on pharmacotherapy 20010601

Title: Treatment options in Waldenström's macroglobulinaemia: the role of the purine analogues.

Journal: Expert opinion on pharmacotherapy 20010601

Title: Hairy cell leukemia.

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