1,3-二氢-1-羟基-2H-苯并咪唑-2-酮 | 53821-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1,3-二氢-1-羟基-2H-苯并咪唑-2-酮
• 英文名称: 1-hydroxy-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 1-hydroxy-1,3-dihydro-benzoimidazol-2-one；2-oxo-2,3-dihydrobenzimidaz-1-ol；1,3-Dihydro-1-hydroxy-2H-benzimidazol-2-one；3-hydroxy-1H-benzimidazol-2-one
• CAS: 53821-11-7
• 化学式: C₇H₆N₂O₂
• 分子量: 150.137
• InChiKey: RNPPCNASSDPHSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  230 °C (decomp)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  1-苯基-3-苯基甲氧基脲 在 palladium 10% on activated carbon 、 氢气 、 lead(IV) tetraacetate 作用下， 以 乙醇 、 氯仿 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 0.58h， 生成 1,3-二氢-1-羟基-2H-苯并咪唑-2-酮
  参考文献：
  名称：

  Synthesis and SAR of 1-Hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of d-Amino Acid Oxidase

  摘要：

  A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of D-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC50 values of the compounds ranging from 70 nM to greater than 100 mu M. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with D-serine to assess their effects on plasma D-serine pharmacokinetics.

  DOI：

  10.1021/ml300212a
• 作为试剂：
  描述：

  4-(Z-氨基)-1-丁醇 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 、 1,3-二氢-1-羟基-2H-苯并咪唑-2-酮 作用下， 生成 benzyl 4-{[2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butylcarbamate
  参考文献：
  名称：

  [EN] FORMULATED AND/OR CO-FORMULATED LIPOSOME COMPOSITIONS CONTAINING TOLL-LIKE RECEPTOR ("TLR") AGONIST PRODRUGS USEFUL IN THE TREATMENT OF CANCER AND METHODS THEREOF
  [FR] COMPOSITIONS LIPOSOMALES FORMULÉES ET/OU CO-FORMULÉES CONTENANT DES PROMÉDICAMENTS AGONISTES DE RÉCEPTEURS DE TYPE TOLL (« TLR ») UTILES DANS LE TRAITEMENT DU CANCER ET MÉTHODES ASSOCIÉES

  摘要：

  本文公开了包含TLR前药和/或TLR脂质基团的配方和/或共配方的脂质体，以及制备脂质体的方法。TLR前药组合物包括药物基团、脂质基团和抑制Toll样受体（例如TLR1/2、TLR4和/或TLR7）的连接单元。可以将TLR前药配方和/或共配方到脂质体中，以提供一种治疗癌症、免疫性疾病和其他疾病的方法，通过利用靶向药物传递载体。

  公开号：

  WO2021126281A1

文献信息

• [EN] NOVEL ETHER LINKED COMPOUNDS AND IMPROVED TREATMENTS FOR CARDIAC AND CARDIOVASCULAR DISEASE<br/>[FR] NOUVEAUX COMPOSÉS À LIAISON ÉTHER ET TRAITEMENTS AMÉLIORÉS POUR LA MALADIE CARDIAQUE ET CARDIOVASCULAIRE
  申请人：UNIV NOTTINGHAM

  公开号：WO2012104659A1

  公开（公告）日：2012-08-09

  A compound of Formula (I), and its pharmaceutically acceptable salt or salts and physiologically hydrolysable derivatives in free form or salt form: wherein R1 is independently selected from F, CI, Br, CN, NH2, OH, CHO, COOH, oxo, C1-4alkyl, C1-4alkoxy, CONH2 (optionally mono- or di-substituted by C1-4alkyl) and SO2NH2, R2 is independently selected from C1-6allkyl substituted by R3 wherein the C1-6alkyl chain optionally comprises one or two heteroatoms select from O; R3 is selected from aryl, C3-6cycloalkyl, C3-6heterocyclyl and C3-6heteroaryl, wherein the heterocyclyl and heteroaryl rings are nitrogen containing; and wherein R3 is optonally substituted by one or more groups selected from R1; n1 is zero or an integer from 1 to 2; n2 is an integer from 1 to 2; and the sum of n1 and 2 is less than or equal to 2; R5 is selected from any group defined for R1 and R2; R6a and R6b are independently selected from H or C1-4alkyl; R7 is independently selected from F, CI, Br, CN, NH2, OH, CHO, COOH, oxo, C1-4alkyl, C1-4alkoxy, CONH2 (optionally mono- or di-substituted by C1-4alkyl) and SO2NH2, Q1, Q2 and Q3 are independently selected from H or any group defined for R1 and R2; or Q1 and Q2 or Q2 and Q3 together form a C5-6heteroaryl or C5-6heterocylclic ring; optionally containing one or two heteroatoms selected from N and O optionally substituted by any group selected from R5; Z is selected from linear C2-3 alkylene; X3 is O; X4 is selected from aryl, a 9-10 membered heteroaryl ring or a 9-10 membered heterocyclic ring, wherein the heteroaryl and heterocyclic rings contain one or more heteroatoms selected from N, and optionally additionally O, and wherein X4 is optionally substituted by one or two oxo moieties and is optionally substituted by one or more groups selected from R7; with the proviso that: (i) when X4 is phenyl then Q1 and Q2 or Q2 and Q3-together form an optionally substituted heteroaryl or heterocylclic ring as defined above; and (ii) when Q1, Q2 and Q3 are independently selected from H or any group defined for R1 and R2 then X4 is not phenyl except when R2 is C1-5alkyl substituted by R3 wherein R3 is C3-6heterocyclyl as defined above.

  公式（I）的化合物及其在自由形式或盐形式中的药学上可接受的盐或可生理水解的衍生物：其中R1独立选择自F、Cl、Br、CN、NH2、OH、CHO、COOH、oxo、C1-4烷基、C1-4烷氧基、CONH2（可选地经C1-4烷基单取代或双取代）和SO2NH2，R2独立选择自由R3取代的C1-6烷基，其中C1-6烷基链可选地包括从O中选择的一个或两个杂原子；R3选择自芳基、C3-6环烷基、C3-6杂环烷基和C3-6杂芳基，其中杂环烷基和杂芳基环含氮；其中R3可选地由R1中选择的一个或多个基团取代；n1为零或1至2的整数；n2为1至2的整数；n1和2的和小于或等于2；R5选择自定义为R1和R2的任何基团；R6a和R6b独立选择自H或C1-4烷基；R7独立选择自F、Cl、Br、CN、NH2、OH、CHO、COOH、oxo、C1-4烷基、C1-4烷氧基、CONH2（可选地经C1-4烷基单取代或双取代）和SO2NH2，Q1、Q2和Q3独立选择自H或自定义为R1和R2的任何基团；或Q1和Q2或Q2和Q3一起形成C5-6杂芳基或C5-6杂环状环；可选地含有从N和O中选择的一个或两个杂原子，可选地由R5中选择的任何基团取代；Z选择自线性C2-3烷基；X3为O；X4选择自芳基、9-10成员杂芳基环或9-10成员杂环状环，其中杂芳基和杂环状环含有从N中选择的一个或多个杂原子，可选地另外含有O，X4可选地由一个或两个oxo基团取代，并可选地由R7中选择的一个或多个基团取代；但条件是：（i）当X4为苯基时，Q1和Q2或Q2和Q3一起形成如上定义的可选取代的杂芳基或杂环状环；和（ii）当Q1、Q2和Q3独立选择自H或自定义为R1和R2的任何基团时，X4不是苯基，除非R2为由R3取代的C1-5烷基，其中R3如上所定义为C3-6杂环烷基。
• Catalytic substitution/cyclization sequences of <i>O</i>-substituted Isocyanates: synthesis of 1-alkoxybenzimidazolones and 1-alkoxy-3,4-dihydroquinazolin-2(1<i>H</i>)-ones
  作者：Qiang Wang、Jing An、Howard Alper、Wen-Jing Xiao、André M. Beauchemin

  DOI：10.1039/c7cc07926e

  日期：——

  used in organic synthesis, given their tendency to undergo side reactions (e.g., trimerization). Herein, we show that masked (blocked) O-isocyanate precursors allow one-pot or cascade reaction sequences featuring base-catalyzed substitution with 2-iodoanilines and 2-iodobenzylamines followed by copper-catalyzed cyclization, to form benzimidazolones and 3,4-dihydroquinazolin-2(1H)-ones. This work shows

  考虑到O-取代的异氰酸酯（O-异氰酸酯）易于发生副反应（例如三聚）的趋势，因此很少用于有机合成中。在这里，我们表明，被掩盖的（封闭的）O-异氰酸酯前体允许一锅或级联反应序列，其特征在于用2-碘苯胺和2-碘苄胺进行碱催化的取代，然后进行铜催化的环化反应，形成苯并咪唑酮和3,4-二氢喹唑啉-2（1 H）-ones。这项工作表明，O-异氰酸酯可以作为合成含羟胺杂环的有效构件。
• SELF-ASSEMBLED NANOSTRUCTURES
  申请人：MAKEIFF Darren Andrew

  公开号：US20110282072A1

  公开（公告）日：2011-11-17

  An alkylated benzimidazolone compound of the formula: wherein at least one of R 1 to R 4 is X—R c , where X represents a linking group, and R a , R b , and R c independently represents substituted or unsubstituted alkyl groups, provided that at least one of R a and R b represents H. The present disclosure provides alkylated benzimidazolone compounds and self-assembled nanostructures formed from alkylated benzimidazolone compounds.

  一种具有以下结构的烷基化苯并咪唑酮化合物：其中R1至R4中至少有一个为X—Rc，其中X代表连接基团，而Ra、Rb和Rc分别代表取代或未取代的烷基基团，但至少有一个为H。本公开提供了烷基化苯并咪唑酮化合物和由烷基化苯并咪唑酮化合物形成的自组装纳米结构。
• Benzimidazole-containing sulfonated polyethersulfones
  申请人：Hung Joyce

  公开号：US20070100131A1

  公开（公告）日：2007-05-03

  Sulfonated polyethersulfones and polymer compositions comprising sulfonated polyethersulfones and at least one inorganic heteropolyacid are useful as proton exchange membranes for fuel cells. The polyethersulfones include structural units derived from at least one biphenol monomer and a monomer of formula I wherein X is O, S or NR 1 ; Y is N or CR 5 ; R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl or substituted arylalkyl, or R 3 and R 4 , taken together, form a 5- or 6-membered substituted or unsubstituted aliphatic or aromatic ring; R 5 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl or substituted arylalkyl; and L is a direct bond or a divalent aromatic linker containing 6-12 carbons

  磺化聚醚砜和包含磺化聚醚砜和至少一种无机杂多酸的聚合物组成物可用作燃料电池的质子交换膜。聚醚砜包括从至少一种联苯单体和式I的单体导出的结构单元，其中X为O、S或NR1；Y为N或CR5；R1、R2、R3和R4独立地为氢、烷基、取代烷基、芳基、取代芳基、烷基芳基、取代烷基芳基、芳基烷基或取代芳基烷基，或R3和R4一起形成一个5-或6-成员的取代或未取代的脂肪族或芳香族环；R5为氢、烷基、取代烷基、芳基、取代芳基、烷基芳基、取代烷基芳基、芳基烷基或取代芳基烷基；L为直接键或含有6-12个碳的二价芳香链节。
• INHIBITORS OF D-AMINO ACID OXIDASE
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20150218156A1

  公开（公告）日：2015-08-06

  D-amino acid oxidase (DAAO) inhibitors and methods of their use, either alone or in combination with D-serine or D-alanine, to facilitate allosteric activation of NMDA receptor-mediated neurotransmission and methods of their use as therapeutic agents for treating a subject afflicted with one or more cognitive-disorders, such as schizophrenia, including subjects suffering from negative symptoms and cognitive impairments, post-traumatic stress disorder (PTSD), or pain, are disclosed.

  本文介绍了D-氨基酸氧化酶（DAAO）抑制剂及其使用方法，无论是单独使用还是与D-丝氨酸或D-丙氨酸结合使用，以促进NMDA受体介导的神经递质的异构激活，并作为治疗剂治疗患有一种或多种认知障碍的受试者，例如精神分裂症，包括患有消极症状和认知障碍的受试者，创伤后应激障碍（PTSD）或疼痛。