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5,8-dihydro-2-(hydroxymethyl)-4-methyl-8-<(4-bromophenyl)methyl>pyrido<2,3-d>pyrimidin-7(6H)-one | 153042-32-1

中文名称
——
中文别名
——
英文名称
5,8-dihydro-2-(hydroxymethyl)-4-methyl-8-<(4-bromophenyl)methyl>pyrido<2,3-d>pyrimidin-7(6H)-one
英文别名
8-(4-bromobenzyl)-2-(hydroxymethyl)-4-methyl-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one;8-[(4-Bromophenyl)methyl]-2-hydroxymethyl-4-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one;8-[(4-bromophenyl)methyl]-2-(hydroxymethyl)-4-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one
5,8-dihydro-2-(hydroxymethyl)-4-methyl-8-<(4-bromophenyl)methyl>pyrido<2,3-d>pyrimidin-7(6H)-one化学式
CAS
153042-32-1
化学式
C16H16BrN3O2
mdl
——
分子量
362.226
InChiKey
OISDAIRYWZUZSI-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):
    1.6
  • 重原子数:
    22
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.31
  • 拓扑面积:
    66.3
  • 氢给体数:
    1
  • 氢受体数:
    4

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
  • 下游产品
    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:
    5,8-dihydro-2-(hydroxymethyl)-4-methyl-8-<(4-bromophenyl)methyl>pyrido<2,3-d>pyrimidin-7(6H)-one四(三苯基膦)钯 manganese(IV) oxide 、 sodium carbonate 作用下, 以 乙醇丙酮甲苯 为溶剂, 生成 8-[2'-(1-tert-Butyl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-4-methyl-7-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-2-carboxylic acid
    参考文献:
    名称:
    Novel human metabolites of the angiotensin-II antagonist tasosartan and their pharmacological effects
    摘要:
    Three novel metabolites of the angiotensin-II (A-II) receptor antagonist tasosartan have been identified in humans, and the syntheses and pharmacologic profiling of these metabolites are reported. Each metabolite bound the human A-II receptor with IC(50)s between 20 and 45 nM. The in vivo effects of these compounds in attenuating the pressor response to angiotensin-II challenge in anesthetized rats were also investigated. An unsaturated diol metabolite exhibited in vivo efficacy at intravenous doses of 1 and 3 mg/kg, while the other metabolites, both carboxylic acids, had no significant effect at the same doses. (C) 2002 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0960-894x(02)00303-7
  • 作为产物:
    描述:
    5,8-dihydro-2-(methoxymethyl)-4-methyl-8-<(4-bromophenyl)methyl>pyrido<2,3-d>pyrimidin-7(6H)-one吡啶碘代三甲硅烷 作用下, 以 氯仿 为溶剂, 反应 30.0h, 以56%的产率得到5,8-dihydro-2-(hydroxymethyl)-4-methyl-8-<(4-bromophenyl)methyl>pyrido<2,3-d>pyrimidin-7(6H)-one
    参考文献:
    名称:
    Pyrido[2,3-d]pyrimidine Angiotensin II Antagonists
    摘要:
    A series of pyrido[2,3-d]pyrimidine angiotensin II (A II) antagonists was synthesized and tested for antagonism of A II. Compounds with a biphenylyltetrazole pharmacophore and small alkyl groups at the 2- and ii-positions Of the pyridopyrimidine ring were found to be the most potent in an AT(1) receptor binding assay and in blocking the A II presser response in anesthetized, ganglion-blocked A II-infused rats. 5,8-Dihydro-2,4-dimethyl-8-[(2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl)methyl] pyrido[2,3-d]pyrimidin-7(6H)-one (4a) was one of the more potent compounds in the binding assay and was the most efficacious compound in the A II-infused rat model. Further study of 4a;in Goldblatt (2K-1C) rats showed the compound to have oral bioavailability and to be an efficacious and potent compound in a high renin form of hypertension.
    DOI:
    10.1021/jm00030a013
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文献信息

  • Substituted pyridopyrimidines and antihypertensives
    申请人:American Home Products Corporation
    公开号:US05466692A1
    公开(公告)日:1995-11-14
    This invention relates to substituted pyridopyrimidinones of general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently H, lower alkyl containing 1 to 6 carbon atoms, hydroxyalkyl containing 1 to 6 carbon atoms, formyl, carbonylalkyl containing 1 to 6 carbon atoms, carboxy, or carboxyalkyl containing 1 to 6 carbon atoms; R.sup.3 and R.sup.4 are independently H, lower alkyl containing 1 to 6 carbon atoms, hydroxy; R.sup.3a and R.sup.4a are H, and when taken together with R.sup.3 and R.sup.4 respectively comprise a carbonyl; with the proviso that at least one of the groups R1 and R.sup.2 must be hydroxyalkyl, formyl, carbonylalkyl containing 1 to 6 carbon atoms, carboxy, or carboxyalkyl containing 1 to 6 carbon atoms; or R.sup.3 and R.sup.4 must be hydroxy or taken together with R.sup.3a and R.sup.4a respectively must comprise a carbonyl; n is 0 to 3; Ar.sup.1 is ##STR2## wherein W is H, lower alkyl containing 1 to 6 carbon atoms, halogen, hydroxy, or lower alkoxy containing 1 to 6 carbon atoms; Ar.sup.2 is ##STR3## wherein X is CO.sub.2 H, CN, or ##STR4## wherein R.sup.5 is H, CH.sub.3, tert-butyl, tri-n-butylstannyl, or triphenylmethyl; and the pharmaceutically acceptable salts thereofuseful for treating hypertension and congestive heart failure, to pharmaceutical compositions, and to methods for production thereof.
    本发明涉及一般式(I)的取代吡啶嘧啶酮:##STR1## 其中R.sup.1和R.sup.2分别为H,含1至6个碳原子的低烷基,含1至6个碳原子的羟基烷基,甲酰基,含1至6个碳原子的羰基烷基,羧基或含1至6个碳原子的羧基烷基;R.sup.3和R.sup.4分别为H,含1至6个碳原子的低烷基,羟基;R.sup.3a和R.sup.4a为H,且与R.sup.3和R.sup.4分别结合成羰基;但必须至少有一组R1和R.sup.2为羟基烷基,甲酰基,含1至6个碳原子的羰基烷基,羧基或含1至6个碳原子的羧基烷基;或R.sup.3和R.sup.4必须为羟基,或与R.sup.3a和R.sup.4a分别结合成羰基;n为0至3;Ar.sup.1为##STR2## 其中W为H,含1至6个碳原子的低烷基,卤素,羟基或含1至6个碳原子的低烷氧基;Ar.sup.2为##STR3## 其中X为CO.sub.2H,CN或##STR4## 其中R.sup.5为H,CH.sub.3,叔丁基,三正丁基锡基或三苯基甲基;以及其药学上可接受的盐,用于治疗高血压和充血性心力衰竭,制药组合物和制备方法。
  • Intermediates useful in the production of pyridopyrimidone angiotensin AII antagonists
    申请人:AMERICAN HOME PRODUCTS CORPORATION
    公开号:EP0863143A1
    公开(公告)日:1998-09-09
    This invention relates to intermediates useful in the production of substituted pyridopyrimidinones of general formula (I): wherein n is 0 to 3; R1 and R2 are, independently, H, C1-C6alkyl, hydroxy(C1-C6alkyl), formyl, carbonyl(C1-C6alkyl), carboxy, or carboxy(C1-C6alkyl); R3 and R4 are, independently, H, C1-C6alkyl, or hydroxy; R3a and R4a are H, or one of -CR3R3a and -CR4R4a is a carbonyl group; with the proviso that at least one of the groups R1 and R2 must be hydroxy(C1-C6alkyl), formyl, carbonyl(C1-C6alkyl), carboxy, or carboxy(C1-C6alkyl); or one of R3 and R4 must be hydroxy; or one of -CR3R3a and -CR4R4a must be a carbonyl group; ; Ar1 is    wherein W is H, C1-C6alkyl, halogen, hydroxy, or C1-C6alkoxy; Ar2 is    wherein X is    wherein R5 is H, CH3, tert-butyl, tri-n-butylstannyl, or triphenylmethyl; or a tautomer of said compound, or a pharmaceutically acceptable salt of said compound or tautomer. The compounds of Formula I are useful for treating hypertension and congestive heart failure. Also disclosed are pharmaceutical compositions containing compounds of Formula I and a pharmaceutically acceptable carrier and methods for production of the compounds of Formula I. Intermediates for making the pharmaceutical useful compounds are also enclosed.
    本发明涉及用于生产通式(I)的取代吡啶嘧啶酮的中间体: 其中 n 为 0 至 3; R1和R2独立地为H、C1-C6烷基、羟基(C1-C6烷基)、甲酰基、羰基(C1-C6烷基)、羧基或羧基(C1-C6烷基); R3 和 R4 独立地为 H、C1-C6 烷基或羟基; R3a 和 R4a 是 H,或 -CR3R3a 和 -CR4R4a 中的一个是羰基; 但 R1 和 R2 中至少有一个基团必须是羟基(C1-C6 烷基)、甲酰基、羰基(C1-C6 烷基)、羧基或羧基(C1-C6 烷基);或 R3 和 R4 中必须有一个是羟基;或 -CR3R3a 和 -CR4R4a 中必须有一个是羰基;; Ar1 是 其中 W 是 H、C1-C6 烷基、卤素、羟基或 C1-C6 烷氧基; Ar2 是 其中 X 是 其中 R5 是 H、CH3、叔丁基、三正丁基锡基或三苯甲基;或所述化合物的同分异构体、 或所述化合物或同系物的药学上可接受的盐。 式 I 的化合物可用于治疗高血压和充血性心力衰竭。还公开了含有式 I 化合物和药学上可接受的载体的药物组合物,以及生产式 I 化合物的方法。
  • Ellingboe John W., Antane Madelene, Nguyen Thomas T., Collini Michael D.,+, J. Med. Chem, 37 (1994) N 4, S 542-550
    作者:Ellingboe John W., Antane Madelene, Nguyen Thomas T., Collini Michael D.,+
    DOI:——
    日期:——
  • Substituted pyridopyrimidines as antihypertensives
    申请人:AMERICAN HOME PRODUCTS CORPORATION
    公开号:EP0618207B1
    公开(公告)日:1999-01-07
  • US5466692A
    申请人:——
    公开号:US5466692A
    公开(公告)日:1995-11-14
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