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4-氯-5-氟喹啉-3-羧酸乙酯 | 655236-30-9

中文名称
4-氯-5-氟喹啉-3-羧酸乙酯
中文别名
——
英文名称
ethyl 5-fluoro-4-chloroquinoline-3-carboxylate
英文别名
Ethyl 4-chloro-5-fluoroquinoline-3-carboxylate
4-氯-5-氟喹啉-3-羧酸乙酯化学式
CAS
655236-30-9
化学式
C12H9ClFNO2
mdl
——
分子量
253.66
InChiKey
WUARCRVHOVVTFY-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.1
  • 重原子数:
    17
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.17
  • 拓扑面积:
    39.2
  • 氢给体数:
    0
  • 氢受体数:
    4

SDS

SDS:8a48f379bbc7963b6d86c10dc448035f
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-氟苯肼4-氯-5-氟喹啉-3-羧酸乙酯乙醇 为溶剂, 生成 9-fluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one
    参考文献:
    名称:
    High affinity central benzodiazepine receptor ligands. Part 3: insights into the pharmacophore and pattern recognition study of intrinsic activities of pyrazolo[4,3- c ]quinolin-3-ones
    摘要:
    Novel 2-phenyl-2,5-dihydropyrazolo[4,3-c]quinolin-3-(3H)-ones (PQs) endowed with high affinity for central benzodiazepine receptor (BzR) were synthesized. In particular, 9-fluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (22) showed binding affinity in the subnanomolar concentration range and proved to be in vitro a potent antagonist. This finding allowed the nature of the hydrogen bonding receptor site H-2 to be established, as located between the N-1 nitrogen of the PQ nucleus and the ortho position of the N-2-aryl group. [S-35]tert-Butylbicyclophosphorothionate ([S-35]TBPS) binding assays and electrophysiological measurements of the effects on GABA-evoked Cl- currents at recombinant human alpha(1)beta(2)gamma(2L) GABA(A) receptors, expressed in Xenopus laevis oocytes, were used to assess the intrinsic activities of a large series of PQs. With the aim of extracting discriminant information and distinguishing BzR ligands with different profiles of efficacy, 51 PQ derivatives, including full and partial agonists, antagonists, and inverse agonists, were analyzed in a multidimensional chemical descriptor space, defined by the lipophilicity parameter CLOG P and 3-D molecular WHIM descriptors, by means of principal component analysis, k-nearest neighbors (k-NN) method, and linear discriminant analysis (LDA). The classification methods were applied to subsets of pairs of efficacy classes, and lipophilicity and 3-D size descriptors were detected as the discriminant variables by a stepwise linear discriminant analysis. LDA proved to be superior to k-NN, especially in classifying PQ ligands (60-84% of success in prediction ability) into categories of efficacies which were contiguous and quite overlapped in the hyperspace of variables. (C) 2003 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/s0968-0896(03)00527-3
  • 作为产物:
    描述:
    4-氟-2-硝基苯胺 在 palladium on activated charcoal 、 盐酸氢气sodium acetate 、 sodium nitrite 、 三氯氧磷 作用下, 以 二苯醚溶剂黄146 为溶剂, 90.0 ℃ 、241.32 kPa 条件下, 反应 27.83h, 生成 4-氯-5-氟喹啉-3-羧酸乙酯
    参考文献:
    名称:
    High affinity central benzodiazepine receptor ligands. Part 3: insights into the pharmacophore and pattern recognition study of intrinsic activities of pyrazolo[4,3- c ]quinolin-3-ones
    摘要:
    Novel 2-phenyl-2,5-dihydropyrazolo[4,3-c]quinolin-3-(3H)-ones (PQs) endowed with high affinity for central benzodiazepine receptor (BzR) were synthesized. In particular, 9-fluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (22) showed binding affinity in the subnanomolar concentration range and proved to be in vitro a potent antagonist. This finding allowed the nature of the hydrogen bonding receptor site H-2 to be established, as located between the N-1 nitrogen of the PQ nucleus and the ortho position of the N-2-aryl group. [S-35]tert-Butylbicyclophosphorothionate ([S-35]TBPS) binding assays and electrophysiological measurements of the effects on GABA-evoked Cl- currents at recombinant human alpha(1)beta(2)gamma(2L) GABA(A) receptors, expressed in Xenopus laevis oocytes, were used to assess the intrinsic activities of a large series of PQs. With the aim of extracting discriminant information and distinguishing BzR ligands with different profiles of efficacy, 51 PQ derivatives, including full and partial agonists, antagonists, and inverse agonists, were analyzed in a multidimensional chemical descriptor space, defined by the lipophilicity parameter CLOG P and 3-D molecular WHIM descriptors, by means of principal component analysis, k-nearest neighbors (k-NN) method, and linear discriminant analysis (LDA). The classification methods were applied to subsets of pairs of efficacy classes, and lipophilicity and 3-D size descriptors were detected as the discriminant variables by a stepwise linear discriminant analysis. LDA proved to be superior to k-NN, especially in classifying PQ ligands (60-84% of success in prediction ability) into categories of efficacies which were contiguous and quite overlapped in the hyperspace of variables. (C) 2003 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/s0968-0896(03)00527-3
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文献信息

  • [EN] 5 -CYANO-4, 6 -DIAMINOPYRIMIDINE OR 6 -AMINOPURINE DERIVATIVES AS PI3K- DELTA INHIBITORS<br/>[FR] DÉRIVÉS DE LA 5-CYANO-4,6-DIAMINOPYRIMIDINE OU DE LA 6-AMINOPURINE EN TANT QU'INHIBITEURS DE LA PI3K-DELTA
    申请人:AMGEN INC
    公开号:WO2012061696A1
    公开(公告)日:2012-05-10
    Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity, The present invention aLso enables methods for treating cancers that are mediated, dependent on or associated with pi 105 activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo- dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia ( T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.
    含有替代双环杂环芳基的化合物及其组合物,用于治疗一般炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠道疾病、炎症性眼部疾病、炎症性或不稳定的膀胱疾病、牛皮癣、伴有炎症成分的皮肤疾病、慢性炎症性疾病,包括但不限于自身免疫性疾病,如系统性红斑狼疮(SLE)、重症肌无力、类风湿关节炎、急性播散性脑脊髓炎、特发性血小板减少性紫癜、多发性硬化症、干燥综合征和自身免疫性溶血性贫血,包括各种过敏症状,本发明还提供了治疗与pi 105活性介导、依赖或相关的癌症的方法,包括但不限于白血病,如急性髓细胞白血病(AML)、髓样增生异常综合征(MDS)、髓增生性疾病(MPD)、慢性髓性白血病(CML)、T细胞急性淋巴细胞白血病(T-ALL)、B细胞急性淋巴细胞白血病(B-ALL)、非霍奇金淋巴瘤(NHL)、B细胞淋巴瘤和实体肿瘤,如乳腺癌。
  • HETEROCYCLIC COMPOUNDS AND THEIR USES
    申请人:Kaizerman Amy
    公开号:US20140031355A1
    公开(公告)日:2014-01-30
    Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity. The present invention also enables methods for treating cancers that are mediated, dependent on or associated with pi 105 activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia (T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.
    含有取代的双环杂芳基和组合物,用于治疗一般性炎症、关节炎、风湿性疾病、骨关节炎、炎性肠病、炎性眼病、炎性或不稳定膀胱疾病、牛皮癣、带有炎症成分的皮肤疾病、包括但不限于自身免疫性疾病如系统性红斑狼疮(SLE)、肌无力、类风湿性关节炎、急性播散性脑脊髓炎、特发性血小板减少性紫癜、多发性硬化症、Sjoegren综合征和自身免疫性溶血性贫血,以及包括所有过敏形式的过敏症。本发明还提供了用于治疗与pi 105活性介导、依赖或相关的癌症的方法,包括但不限于白血病,如急性髓性白血病(AML)、骨髓增生异常综合征(MDS)、骨髓增生性疾病(MPD)、慢性髓性白血病(CML)、T细胞急性淋巴细胞白血病(T-ALL)、B细胞急性淋巴细胞白血病(B-ALL)、非霍奇金淋巴瘤(NHL)、B细胞淋巴瘤和实体瘤,如乳腺癌。
  • 5 -CYANO-4, 6 -DIAMINOPYRIMIDINE OR 6 -AMINOPURINE DERIVATIVES AS PI3K- DELTA INHIBITORS
    申请人:Amgen Inc.
    公开号:EP2635565A1
    公开(公告)日:2013-09-11
  • High affinity central benzodiazepine receptor ligands. Part 3: insights into the pharmacophore and pattern recognition study of intrinsic activities of pyrazolo[4,3- c ]quinolin-3-ones
    作者:Andrea Carotti、Cosimo Altomare、Luisa Savini、Luisa Chiasserini、Cesare Pellerano、Maria P. Mascia、Elisabetta Maciocco、Fabio Busonero、Manuel Mameli、Giovanni Biggio、Enrico Sanna
    DOI:10.1016/s0968-0896(03)00527-3
    日期:2003.11
    Novel 2-phenyl-2,5-dihydropyrazolo[4,3-c]quinolin-3-(3H)-ones (PQs) endowed with high affinity for central benzodiazepine receptor (BzR) were synthesized. In particular, 9-fluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (22) showed binding affinity in the subnanomolar concentration range and proved to be in vitro a potent antagonist. This finding allowed the nature of the hydrogen bonding receptor site H-2 to be established, as located between the N-1 nitrogen of the PQ nucleus and the ortho position of the N-2-aryl group. [S-35]tert-Butylbicyclophosphorothionate ([S-35]TBPS) binding assays and electrophysiological measurements of the effects on GABA-evoked Cl- currents at recombinant human alpha(1)beta(2)gamma(2L) GABA(A) receptors, expressed in Xenopus laevis oocytes, were used to assess the intrinsic activities of a large series of PQs. With the aim of extracting discriminant information and distinguishing BzR ligands with different profiles of efficacy, 51 PQ derivatives, including full and partial agonists, antagonists, and inverse agonists, were analyzed in a multidimensional chemical descriptor space, defined by the lipophilicity parameter CLOG P and 3-D molecular WHIM descriptors, by means of principal component analysis, k-nearest neighbors (k-NN) method, and linear discriminant analysis (LDA). The classification methods were applied to subsets of pairs of efficacy classes, and lipophilicity and 3-D size descriptors were detected as the discriminant variables by a stepwise linear discriminant analysis. LDA proved to be superior to k-NN, especially in classifying PQ ligands (60-84% of success in prediction ability) into categories of efficacies which were contiguous and quite overlapped in the hyperspace of variables. (C) 2003 Elsevier Ltd. All rights reserved.
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