(R)-4,5-dihydro-4-[2-(methylthio)ethyl]-2-phenyl-1,3-oxazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4,5-dihydro-4-[2-(methylthio)ethyl]-2-phenyl-1,3-oxazole
• 英文别名: (R)-4-(2-methylthioethyl)-2-phenyl-4,5-dihydrooxazole；(4R)-4-(2-methylsulfanylethyl)-2-phenyl-4,5-dihydro-1,3-oxazole
• 化学式: C₁₂H₁₅NOS
• 分子量: 221.323
• InChiKey: AOSAIENAYXFNEV-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4,5-dihydro-4-[2-(methylthio)ethyl]-2-phenyl-1,3-oxazole 在 盐酸 、 溶剂黄146 作用下， 反应 112.5h， 生成 (R)-N-(tetrahydrothiophen-3-yl)benzoylamine
  参考文献：
  名称：

  Structure–activity relationships of adenosines with heterocyclic N6-substituents

  摘要：

  Two series of N-6-substituted adenosines with monocyclic and bicyclic N-6 substituents containing a heteroatom were synthesized in good yields. These derivatives were assessed for their affinity ([H-3]CPX), potency, and intrinsic activity (cAMP accumulation) at the A, adenosine receptor in DDT1 MF-2 cells. In the monocyclic series, the N-6-tetrahydrofuran-3-yl and thiolan-3-yl adenosines (1 and 26, respectively) were found to possess similar activities, whereas the corresponding selenium analogue 27 was found to be more potent. A series of nitrogen containing analogues showed varying properties, N-6-((3R)-1-benzyloxycarbonylpyrrolidin-3-yl)adenosine (30) was the most potent at the AIAR; IC50 = 3.2 nM. In the bicyclic series, the effect of a 7-azabicyclo[2.2.1]heptan-2-yl substituent in the N-6-position was explored. N6- (7-Azabicyclo[2.2.1] heptan-2-yl)adeno sine (38) proved to be a reasonably potent A, agonist (K-i = 51 nM, IC50 = 35 nM) while further substitution on the 7 ''-nitrogen with tert-butoxycarbonyl (31, IC50 = 2.5 nM) and 2-bromobenzyloxycarbonyl (34, IC50 = 9.0 nM) gave highly potent A(1)AR agonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.028
• 作为产物：
  描述：

  D-蛋氨醇 、 苯甲腈 在 溴化锌 氮气 、 水 、 Brine 、 magnesium sulfate 、 resultant crude product 、 silica gel 、 ethyl acetate n-hexane 作用下， 反应 90.0h， 以to give (R)-4-(2-methylthioethyl)-2-phenyl-4,5-dihydrooxazole (3.94 g, yield: 48.6%) as a colorless oil的产率得到(R)-4,5-dihydro-4-[2-(methylthio)ethyl]-2-phenyl-1,3-oxazole
  参考文献：
  名称：

  PYRAZOLO[1,5-A] PYRIMIDINE COMPOUNDS AS CB1 RECEPTOR ANTAGONIST

  摘要：

  一种具有CB1受体拮抗活性的吡唑并[1,5-a]嘧啶化合物，其化学式为[I]：其中R1和R2相同或不同，且每个都是可选取代的芳基基团等，R0为氢、烷基基团等，E为—C(═O)—或—SO2—，R为式[i]、[ii]或[iii]等的基团：环A为C3-8环烷基团，可选地融合到苯环或苯环上，Q为单键或亚甲基基团，环B为4-至7-成员的脂肪族杂环基团，所述环基团通过其环碳原子与相邻的氮原子结合，X为硫原子等，R3为可选取代的烷基基团，R4为氢原子、烷基基团等，RA和RB中的一个为烷基基团等，另一个为氢、烷基基团等，或其药学上可接受的盐。

  公开号：

  US20120202992A1

文献信息

• PYRAZOLO[1,5-A] PYRIMIDINE COMPOUNDS AS CB1 RECEPTOR ANTAGONIST
  申请人：Tanimoto Koichi

  公开号：US20090258867A1

  公开（公告）日：2009-10-15

  The present invention provides a pyrazolo[1,5-a]pyrimidine compound, having CB1 receptor-antagonizing activity, of the following formula [I]: in which R 1 and R 2 are the same or different and each an optionally substituted aryl group etc, R 0 is hydrogen atom, an alkyl group etc, E is a group of the formula: —C(═O)— or —SO 2 —, R is a group of the following formula [i], [ii] or [iii] etc: Ring A is (a) a C 3-8 cycloalkyl group optionally fused to a benzene ring or (b) a benzene ring, Q is a single bond or a methylene group, Ring B is a 4- to 7-membered aliphatic heterocyclic group, said cyclic group binding via its ring-carbon atom to the adjacent nitrogen atom, X is sulfur atom etc, R 3 is an alkyl group optionally substituted by an alkylthio group, R 4 is hydrogen atom, an alkyl group etc, one of R A and R B is an alkyl group etc, and the other is hydrogen atom, an alkyl group etc, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有CB1受体拮抗活性的吡唑并[1,5-a]嘧啶化合物，其化学式[I]如下：其中，R1和R2相同或不同，分别是可选取代的芳基等；R0是氢原子，烷基等；E是以下式子的基团：—C(═O)—或—SO2—；R是以下式子[i]、[ii]或[iii]等的基团：环A是(a)一个C3-8环烷基，可选地融合到苯环上，或(b)一个苯环；Q是单键或亚甲基基团；环B是一个4-7个成员的脂肪族杂环基团，该环基团通过其环碳原子与相邻的氮原子结合；X是硫原子等；R3是可选取代的烷基，可以是烷基硫基等；R4是氢原子，烷基等；RA和RB中的一个是烷基等，另一个是氢原子，烷基等，或其药学上可接受的盐。
• Pyrazolo[1,5-A]Pyrimidine Compounds
  申请人：Moritani Yasunori

  公开号：US20090069298A1

  公开（公告）日：2009-03-12

  The present invention relates to a novel pyrazolo[1,5-a]pyrimidine compound of the formula [I]: wherein R 1 and R 2 are the same or different and an optionally substituted aryl group etc. Q is single bond, a methylene group or a group of the formula: —N(R Q )—, R Q is an alkyl group, Ring A is a substituted pyrazole ring fused to the adjacent pyrimidine ring having the following formula (A), (B) or (C), R 3 and R 4 are the same or different and a hydrogen atom, a cyano group etc. E is one of the following groups (i) to (v): R 00 is an alkyl group, Q 1 is a single bond etc., Q 2 is a single bond or an alkylene group, one of R 5 and R 6 is a hydrogen atom or an alkyl group and the other is an alkyl group etc., one of R 50 and R 60 is a hydrogen atom or an alkyl group and the other is a hydrogen atom, an alkyl group etc., R 51 is an alkyl group or an optionally substituted arylsulfonyl group, R 61 is an alkylamino group or an azido group, or a pharmaceutically acceptable salt thereof.

  本发明涉及一种新型吡唑并[1,5-a]嘧啶化合物，其化学式为[I]：其中R1和R2相同或不同，可以是任选取代芳基等；Q是单键，亚甲基基团或式子：—N(RQ)—，RQ是烷基基团；环A是一个取代的吡唑环与相邻的嘧啶环融合，具有以下式子(A)、(B)或(C)：其中R3和R4相同或不同，可以是氢原子、氰基等；E是以下式子(i)至(v)中的一种：其中R00是烷基基团，Q1是单键等，Q2是单键或烷基烃基团，R5和R6中的一个是氢原子或烷基基团，另一个是烷基基团等，R50和R60中的一个是氢原子或烷基基团，另一个是氢原子、烷基基团等，R51是烷基基团或任选取代的芳基磺酰基团，R61是烷基氨基基团或叠氮基团，或其药学上可接受的盐。
• Phenyl and Benzodioxinyl Substituted Indazoles Derivatives
  申请人：Berger Markus

  公开号：US20100087489A1

  公开（公告）日：2010-04-08

  A compound of formula Ia: The present invention relates to novel indazolyl derivatives, to pharmaceutical compositions comprising such derivatives, to processes for preparing such novel derivatives and to the use of such derivatives as medicaments

  一种化学式为Ia的化合物：本发明涉及新型吲哚基衍生物，涉及包含这种衍生物的药物组合物，涉及制备这种新型衍生物的方法以及将这种衍生物用作药物的用途。
• Pyrazolo[1,5-A] pyrimidine compounds as CB1 receptor antagonist
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US08163759B2

  公开（公告）日：2012-04-24

  The present invention provides a pyrazolo[1,5-a]pyrimidine compound, having CB1 receptor-antagonizing activity, of the following formula [I]: in which R1 and R2 are the same or different and each an optionally substituted aryl group etc, R0 is hydrogen atom, an alkyl group etc, E is a group of the formula: —C(═O)— or —SO2—, R is a group of the following formula [i], [ii]or [iii] etc: Ring A is (a) a C3-8 cycloalkyl group optionally fused to a benzene ring or (b) a benzene ring, Q is a single bond or a methylene group, Ring B is a 4- to 7-membered aliphatic heterocyclic group, said cyclic group binding via its ring-carbon atom to the adjacent nitrogen atom, X is sulfur atom etc, R3 is an alkyl group optionally substituted by an alkylthio group, R4 is hydrogen atom, an alkyl group etc, one of RA and RB is an alkyl group etc, and the other is hydrogen atom, an alkyl group etc, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有CB1受体拮抗活性的吡唑并[1,5-a]嘧啶化合物，其化学式[I]如下：其中，R1和R2相同或不同，分别为可选择取代的芳基基团等，R0为氢原子、烷基基团等，E为下式的基团：—C(═O)—或—SO2—，R为下式的基团[i]、[ii]或[ iii]等：环A为(a)一个C3-8环烷基团，可选择与苯环融合，或(b)一个苯环，Q为单键或亚甲基基团，环B为一个4-至7-成员的脂环杂环基团，所述环基团通过其环碳原子与相邻的氮原子结合，X为硫原子等，R3为可选择取代的烷基基团，其中该烷基基团被烷基硫基取代，R4为氢原子、烷基基团等，RA和RB中的一个为烷基基团等，另一个为氢原子、烷基基团等，或其药学上可接受的盐。
• Pyrazolo[1,5-A]pyrimidine compounds
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US08188097B2

  公开（公告）日：2012-05-29

  The present invention relates to a novel pyrazolo[1,5-a]pyrimidine compound of the formula [I]: wherein R1 and R2 are the same or different and an optionally substituted aryl group etc. Q is single bond, a methylene group or a group of the formula: —N(RQ)—, RQ is an alkyl group, Ring A is a substituted pyrazole ring fused to the adjacent pyrimidine ring having the following formula (A), (B) or (C), R3 and R4 are the same or different and a hydrogen atom, a cyano group etc. E is one of the following groups (i) to (v): R00 is an alkyl group, Q1 is a single bond etc., Q2 is a single bond or an alkylene group, one of R5 and R6 is a hydrogen atom or an alkyl group and the other is an alkyl group etc., one of R50 and R60 is a hydrogen atom or an alkyl group and the other is a hydrogen atom, an alkyl group etc., R51 is an alkyl group or an optionally substituted arylsulfonyl group, R61 is an alkylamino group or an azido group, or a pharmaceutically acceptable salt thereof.

  本发明涉及一种新的嘧唑并[1,5-a]嘧啶化合物，其化学式为[I]，其中R1和R2相同或不同，可选取取代基的芳基等。Q为单键，亚甲基基或式子为：—N(RQ)—的基团，RQ为烷基。环A是一个取代的嘧唑环，与相邻的嘧啶环融合，其具有以下式子（A）、（B）或（C）：R3和R4相同或不同，可选取氢原子，氰基等。E是以下化合物组之一：（i）至（v）中的一种：R00为烷基，Q1为单键等，Q2为单键或烷基亚基，R5和R6中的一个为氢原子或烷基，另一个为烷基等，R50和R60中的一个为氢原子或烷基，另一个为氢原子，烷基等，R51为烷基或可选取取代基的芳基磺酰基，R61为烷基氨基基团或偶氮基团，或其药学上可接受的盐。