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1-(3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

中文名称
——
中文别名
——
英文名称
1-(3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
英文别名
(2 inverted exclamation mark R)-2 inverted exclamation mark-Deoxy-2 inverted exclamation mark-fluoro-2 inverted exclamation mark-methyluridine;1-[3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidine-2,4-dione
1-(3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione化学式
CAS
——
化学式
C10H13FN2O5
mdl
——
分子量
260.222
InChiKey
ARKKGZQTGXJVKW-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):
    -1.1
  • 重原子数:
    18
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.6
  • 拓扑面积:
    99.1
  • 氢给体数:
    3
  • 氢受体数:
    6

上下游信息

  • 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:
    参考文献:
    名称:
    酶催化手性前体对抗病毒前药的动力学拆分。
    摘要:
    核苷类似物是用于治疗病毒感染和癌症的最常用药物之一。核苷类似物的治疗效果可通过磷酸化显着提高。ProTide方法是使用磷酸化的核苷开发的,该磷酸化的核苷通过与氨基酸和苯酚形成手性磷中心的酯化作用而被掩盖。ProTides的生物活性部分取决于磷的立体化学,因此,必须开发有效的方法来化学合成和分离非对映异构纯ProTides。手性肽通常是通过从具有适当核苷类似物的手性氨基磷酸酯前体中直接取代不稳定的苯酚(对硝基苯酚或五氟苯酚)而合成的。产生这些手性产物的能力取决于手性氨基磷酸酯前体的合成。来自假单胞菌的磷酸三酯酶(PTE)以其高立体选择性和广泛的底物特性而闻名。从酶进化文库中筛选PTE变体能够鉴定可以立体选择性地水解手性氨基磷酸酯前体的PTE变体。变体G60A-PTE对RP异构体的水解表现出165倍的偏好,而变体In1W-PTE对SP异构体的水解表现出1400倍的偏好。使用这些PTE突变体,可
    DOI:
    10.1021/acs.biochem.9b00530
点击查看最新优质反应信息

文献信息

  • Macroheterocyclic nucleoside derivatives and their analogues, production and use thereof
    申请人:Ivachtchenko Alexandre Vasilievich
    公开号:US20180099989A1
    公开(公告)日:2018-04-12
    Nucleosides and nucleotides (nucleos(t)ides) have been in clinical use for almost 50 years and have become cornerstones of treatment for patients with viral infections or cancer. The approval of several additional drugs over the past decade demonstrates that this family still possesses strong potential. Therefore nucleos(t)ide are of great interest as promising chemotherapeutic agents, including: 2′-deoxy-L-uridine (CAS No 31501-19-6), 2′-deoxy-D-uridine (CAS No 951-78-0), telbivudine (CAS No 3424-98-4), zidovudine (AZT, CAS No 30516-87-1), trifluridine (CAS No 70-00-8), clevudine (CAS No 163252-36-6), PSI-6206 (CAS No 863329-66-2), 2′-(5)-2′-chloro-2′-deoxy-2′-fluorouridine (CAS No 1673560-41-2), ND06954 (CAS No 114248-23-6), stavudine (CAS No 3056-17-5), 5-ethynyltavudine (Festinavir, CAS No 634907-30-5), torcitabine (CAS No 40093-94-5), (−)-beta-D-(2R,4R)-dioxolane-thymine (DOT, 1-((2R,4R)-2-(hydroxymethyl)-1,3-dioxolan-4-yl)-5-methyl-2,4 (1H,3H)-pyrimidinedione, CAS No. 127658-07-5), 2-(6-amino-purin-9-yl)-ethanol (CAS No 707-99-3), 2′-C-methylcytidine (CAS No 20724-73-6), PSI-6130 (CAS No 817204-33-4), gemcitabine (CAS No 95058-81-4), 2′-chloro-2′-deoxy-2′-fluorocytidine (CAS No 1786426-19-4), 2′,2′-dichloro-2′-deoxycytidine (CAS No 1703785-65-2), 2′-C-methylcytidine (CAS No 20724-73-6), PSI-6130 (CAS No 817204-33-4), lamivudine (3TC, CAS No 134678-17-4), emtricitabine (CAS No 143491-57-0), 2′-deoxyadenosine (CAS No 958-09-8), 2′-deoxy-β-L-adenosine (CAS No 14365-45-8), 2′-deoxy-4′-C-ethynyl-2-fluoroadenosine (CAS No 865363-93-5), didanosine (CAS No 69655-05-6), entecavir (CAS No 209216-23-9), FMCA (CAS No 1307273-70-6), dioxolane-G (DOG, CAS No 145514-01-8), β-D-2′-deoxy-2′-(R)-fluoro-2′-β-C-methylguanosine (CAS No 817204-45-8), abacavir (ABC, CAS No 136470-78-5), dioxolane-A (DOA, CAS #145514-02-9), [(2R,4R)-4-(6-cyclopropylamino-purin-9-yl)-[1,3]dioxolan-2-yl]-methanol (CAS No 1446751-04-7), amdoxovir (AMDX, CAS No 145514-04-1), (R)-1-(6-amino-purin-9-yl)-propan-2-ol (CAS No 14047-28-0), and [(2S,5R)-5-(6-amino-purin-9-yl)-4-fluoro-2,5-dihydro-furan-2-yl]-methanol. Macroheterocyclic nucleoside derivative and its analogue of the general formula 1 or general formula 2, a stereoisomer, isotope-enriched analogue, pharmaceutically acceptable salt, hydrate, solvate, or crystalline or polymorphic form thereof, wherein: Ar is aryl or hetaryl; R 1 and R 2 are not necessarily the same substituents selected from H, F, Cl, CH 3 , OH; R 3 is H or CH 3 ; X is oxygen or ethanediyl-1,1 (C═CH 2 ); Y is CH(R 4 )(CH 2 ) k , CH(R 4 )(CH 2 ) m C(O)O(CH 2 ) n ; R 4 is H or CH 3 ; k has a value from zero to six; m has a value from zero to two; n has a value of one to four; Q is a radical selected from Q1-Q4; wherein: R 5 is the substituent selected from H, F, Cl, CH 3 , OH; the arrow (→) indicates the location, joined by Q1-Q4.
    核苷和核苷酸(核苷(t)酸)已经在临床上使用了近50年,已成为治疗病毒感染或癌症患者的治疗基石。过去十年批准了几种额外的药物,表明这个家族仍然具有强大的潜力。因此,核苷(t)酸作为有前途的化疗药物具有很大的吸引力,包括:2'-脱氧-L-尿苷(CAS号31501-19-6)、2'-脱氧-D-尿苷(CAS号951-78-0)、替比夫定(CAS号3424-98-4)、阿司匹林(AZT,CAS号30516-87-1)、三氟胸苷(CAS号70-00-8)、克雷胸苷(CAS号163252-36-6)、PSI-6206(CAS号863329-66-2)、2'-(5)-2'-氯-2'-脱氧-2'-氟尿苷(CAS号1673560-41-2)、ND06954(CAS号114248-23-6)、司他夫定(CAS号3056-17-5)、5-乙炔基司他夫定(费司那韦,CAS号634907-30-5)、托西他滨(CAS号40093-94-5)、(-)-β-D-(2R,4R)-二氧杂环己嘧啶(DOT,1-((2R,4R)-2-(羟甲基)-1,3-二氧杂环己-4-基)-5-甲基-2,4(1H,3H)-嘧啶二酮,CAS号127658-07-5)、2-(6-氨基嘌呤-9-基)-乙醇(CAS号707-99-3)、2'-C-甲基胞苷(CAS号20724-73-6)、PSI-6130(CAS号817204-33-4)、吉西他滨(CAS号95058-81-4)、2'-氯-2'-脱氧-2'-氟胞苷(CAS号1786426-19-4)、2',2'-二氯-2'-脱氧胞苷(CAS号1703785-65-2)、2'-C-甲基胞苷(CAS号20724-73-6)、PSI-6130(CAS号817204-33-4)、拉米夫定(3TC,CAS号134678-17-4)、恩替卡韦(CAS号143491-57-0)、2'-脱氧腺苷(CAS号958-09-8)、2'-脱氧-β-L-腺苷(CAS号14365-45-8)、2'-脱氧-4'-C-乙炔基-2-氟腺苷(CAS号865363-93-5)、地达诺辛(CAS号69655-05-6)、恩替卡韦(CAS号209216-23-9)、FMCA(CAS号1307273-70-6)、二氧杂环己胞苷(DOG,CAS号145514-01-8)、β-D-2'-脱氧-2'-(R)-氟-2'-β-C-甲基鸟苷(CAS号817204-45-8)、阿巴卡韦(ABC,CAS号136470-78-5)、二氧杂环己-A(DOA,CAS号145514-02-9)、[(2R,4R)-4-(6-环丙基氨基嘌呤-9-基)-[1,3]二氧杂环己-2-基]-甲醇(CAS号1446751-04-7)、阿姆多氧韦(AMDX,CAS号145514-04-1)、(R)-1-(6-氨基嘌呤-9-基)-丙醇(CAS号14047-28-0)、和[(2S,5R)-5-(6-氨基嘌呤-9-基)-4-氟-2,5-二氢呋喃-2-基]-甲醇。 宏环核苷衍生物及其一般式1或一般式2的类似物,立体异构体,同位素富集类似物,药学上可接受的盐,水合物,溶剂合物,或其结晶或多形式, 其中: Ar是芳基或杂芳基; R 1 和R 2 不一定相同,选自H,F,Cl,CH 3 ,OH的取代基; R 3 是H或CH 3 ; X是氧或乙烯二基-1,1(C═CH 2 ); Y是CH(R 4 )(CH 2 ) k ,CH(R 4 )(CH 2 ) m C(O)O(CH 2 ) n ; R 4 是H或CH 3 ; k的值从零到六; m的值从零到二; n的值从一到四; Q是从Q1-Q4中选择的基团; 其中:R 5 是选自H,F,Cl,CH 3 ,OH的取代基; 箭头(→)表示位置,由Q1-Q4连接。
  • [EN] PHOSPHORAMIDATE NUCLEOSIDE PRODRUG FOR TREATING VIRAL DISEASES AND CANCER, PROCESSES FOR THEIR PREPARATION AND THEIR USE<br/>[FR] PROMÉDICAMENT NUCLÉOSIDE PHOSPHORAMIDATE DESTINÉ AU TRAITEMENT DES MALADIES VIRALES ET DU CANCER, LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION
    申请人:IVACHTCHENKO ALEXANDRE VASILIEVICH
    公开号:WO2018022221A1
    公开(公告)日:2018-02-01
    The present invention pertains to chemotherapeutic agents and their use for treating viral and cancerous diseases. These compounds are inhibitors of HCV NS5B polymerase, HBV DNA polymerase and, HIV-1 reverse transcriptase (RT) inhibitor, and for treatment of hepatitis B and C infection in mammals. These compounds are also of interest for the treatment of cancer. The phosphoramidate nucleoside prodrug of the general formula (1), a stereoisomer, isotope-enriched analogue, pharmaceutically acceptable salt, hydrate, solvate, or crystalline or polymorphic form thereof, formula (1) wherein: Ar is aryl or hetaryl; R1 is H or CH3, R2 is the substituent selected from OCH2CH=CH2, OCH2CH≡CH, OCH2CH2CH2OCH3, formula (2), formula (3) or formula (4), R3 is H or CH3; R4 is OH, OR5, NR6R7; R5 is C1-C4-alkyl; R6 and R7 are not necessarily the same substituents selected from H or CH3, Z = O, or NH; an arrow (→) indicates the place of substituent connection; Nuc is formula (5) or (6); R8 and R9 are not necessarily the same substituents selected from H, F, Cl, CH3 or OH provided when continuous line and its accompanying dotted line ( ) together are the single carbon-carbon (C-C) bond or R8 and R9 are hydrogen provided when continuous line and its accompanying dotted line ( ) together are the double carbon-carbon bond (C=C); R10 is the substituent selected from R10.1- R10.5; R10.1 R10.2 R10.4 R10.5 ; R11 is the substituent selected from H, F, CI, CH3, or CF3; R12 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl; X is oxygen or ethanediyl-1,1 (C=CH2); Y is O, S, CH2, or HO-CH group provided when continuous line and its accompanying dotted line (formula 7) together are the single carbon-carbon (C-C) bond or Y is CH group provided when continuous line and its accompanying dotted line (formula 7) together are the double carbon-carbon bond (C=C), and compound of the general formula (1), stereoisomers, isotope-enriched analogues, pharmaceutically acceptable salts, hydrates, solvates, or crystalline or polymorphic forms thereof, wherein: Ar is aryl or hetaryl; R1 is H or CH3; R2 is isopropyl; Nuc is formula (8), (9) or (10).
    本发明涉及化疗药物及其用于治疗病毒性和癌症疾病的用途。这些化合物是HCV NS5B聚合酶、HBV DNA聚合酶和HIV-1逆转录酶(RT)抑制剂,用于治疗哺乳动物中的乙型和丙型肝炎感染。这些化合物也对癌症治疗具有兴趣。通用式(1)的磷酰胺核苷前药的立体异构体、同位素富集类似物、药学上可接受的盐、水合物、溶剂合物或晶体或多形式,式(1)其中:Ar为芳基或杂芳基;R1为H或CH3,R2为从OCH2CH=CH2、OCH2CH≡CH、OCH2CH2CH2OCH3、式(2)、式(3)或式(4)中选择的取代基,R3为H或CH3;R4为OH、OR5、NR6R7;R5为C1-C4-烷基;R6和R7不一定相同,选择自H或CH3的取代基,Z=O或NH;箭头(→)表示取代基连接的位置;Nuc为式(5)或(6);R8和R9不一定相同,选择自H、F、Cl、CH3或OH,提供当连续线及其相应的虚线()一起为单碳-碳(C-C)键时,或R8和R9为氢,提供当连续线及其相应的虚线()一起为双碳-碳键(C=C)时;R10为从R10.1-R10.5中选择的取代基;R10.1 R10.2 R10.4 R10.5;R11为从H、F、Cl、CH3或CF3中选择的取代基;R12为氢、C1-C4-烷基或C3-C6-环烷基;X为氧或乙烯二基-1,1(C=CH2);Y为O、S、CH2或HO-CH基,提供当连续线及其相应的虚线(式7)一起为单碳-碳(C-C)键时,或Y为CH基,提供当连续线及其相应的虚线(式7)一起为双碳-碳键(C=C)时,以及通用式(1)的化合物、立体异构体、同位素富集类似物、药学上可接受的盐、水合物、溶剂合物或晶体或多形式,其中:Ar为芳基或杂芳基;R1为H或CH3;R2为异丙基;Nuc为式(8)、(9)或(10)。
  • [EN] PROCESS FOR PREPARING PHOSPHORAMIDATE DERIVATIVES OF NUCLEOSIDE COMPOUNDS FOR TREATMENT OF VIRAL INFECTIONS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS PHOSPHORAMIDATÉS DE COMPOSÉS NUCLÉOSIDIQUES UTILISABLES EN VUE DU TRAITEMENT D'INFECTIONS VIRALES
    申请人:BRISTOL MYERS SQUIBB CO
    公开号:WO2014047117A1
    公开(公告)日:2014-03-27
    Processes for the production of nucleoside phosphoramidate compounds having the following Formula I are provided.
    提供生产以下化学式I的核苷酸磷酰胺化合物的工艺。
  • 2'-Fluoronucleoside phosphonates as antiviral agents
    申请人:Shi Junxing
    公开号:US20070225249A1
    公开(公告)日:2007-09-27
    The present invention includes compounds and compositions of R -2′-fluoronucleoside phosphonates, as well as methods to treat HIV, HBV, HCV or abnormal cellular proliferation comprising administering said compounds or compositions.
    本发明涉及R-2'-氟核苷酸膦酸酯化合物和组合物,以及使用该化合物或组合物治疗HIV、HBV、HCV或异常细胞增殖的方法。
  • MODIFIED FLUORINATED NUCLEOSIDE ANALOGUES
    申请人:CLARK JEREMY
    公开号:US20080070861A1
    公开(公告)日:2008-03-20
    The disclosed invention provides compositions and methods of treating a Flaviviridae infection, including hepatitis C virus, West Nile Virus, yellow fever virus, and a rhinovirus infection in a host, including animals, and especially humans, using a (2′R)-2′-deoxy-2′-fluoro-2′-C-methyl nucleosides, or a pharmaceutically acceptable salt or prodrug thereof.
    本公开发明提供了用(2′R)-2′-脱氧-2′-氟-2′-C-甲基核苷或其药学上可接受的盐或前药治疗Flaviviridae感染的组合物和方法,包括丙型肝炎病毒、西尼罗病毒、黄热病毒和鼻病毒感染,在宿主中,包括动物,特别是人类。
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