N-(2-morpholinophenyl)formamide | 91181-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-(2-morpholinophenyl)formamide
• 英文别名: 1-<2-Formamino-phenyl>-morpholin；N-(2-morpholin-4-yl-phenyl)-formamide；N-(2-morpholin-4-ylphenyl)formamide
• CAS: 91181-03-2
• 化学式: C₁₁H₁₄N₂O₂
• mdl: MFCD03163589
• 分子量: 206.244
• InChiKey: JMSTUHRGWFUEMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-morpholinophenyl)formamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以51 %的产率得到N-methyl-2-morpholinoaniline
  参考文献：
  名称：

  Synthesis and in vitro Metabolic Stability of Sterically Shielded Antimycobacterial Phenylalanine Amides

  摘要：

  Nα‐aroyl‐N‐aryl‐phenylalanine amides (AAPs) are RNA polymerase inhibitors with activity against Mycobacterium tuberculosis and non‐tuberculous mycobacteria. We observed that AAPs rapidly degrade in microsomal suspensions, suggesting that avoiding hepatic metabolism is critical for their effectiveness in vivo. As both amide bonds are potential metabolic weak points of the molecule, we synthesized 16 novel AAP analogs in which the amide bonds are shielded by methyl or fluoro substituents in close proximity. Some derivatives show improved microsomal stability, while being plasma‐stable and non‐cytotoxic. In parallel with the metabolic stability studies, the antimycobacterial activity of the AAPs against Mycobacterium tuberculosis, Mycobacterium abscessus, Mycobacterium avium and Mycobacterium intracellulare was determined. The stability data are discussed in relation to the antimycobacterial activity of the panel of compounds and reveal that the concept of steric shielding of the anilide groups by a fluoro substituent has the potential to improve the stability and bioavailability of AAPs.

  DOI：

  10.1002/cmdc.202300593
• 作为产物：
  描述：

  甲酸 、 4-2-胺苯基吗啉 在 sodium formate 作用下， 以79 %的产率得到N-(2-morpholinophenyl)formamide
  参考文献：
  名称：

  Synthesis and in vitro Metabolic Stability of Sterically Shielded Antimycobacterial Phenylalanine Amides

  摘要：

  Nα‐aroyl‐N‐aryl‐phenylalanine amides (AAPs) are RNA polymerase inhibitors with activity against Mycobacterium tuberculosis and non‐tuberculous mycobacteria. We observed that AAPs rapidly degrade in microsomal suspensions, suggesting that avoiding hepatic metabolism is critical for their effectiveness in vivo. As both amide bonds are potential metabolic weak points of the molecule, we synthesized 16 novel AAP analogs in which the amide bonds are shielded by methyl or fluoro substituents in close proximity. Some derivatives show improved microsomal stability, while being plasma‐stable and non‐cytotoxic. In parallel with the metabolic stability studies, the antimycobacterial activity of the AAPs against Mycobacterium tuberculosis, Mycobacterium abscessus, Mycobacterium avium and Mycobacterium intracellulare was determined. The stability data are discussed in relation to the antimycobacterial activity of the panel of compounds and reveal that the concept of steric shielding of the anilide groups by a fluoro substituent has the potential to improve the stability and bioavailability of AAPs.

  DOI：

  10.1002/cmdc.202300593

文献信息

• 2,3-Dihydro-6-nitroimidazo[2,1-b]oxazoles
  申请人：Tsubouchi Hidetsugu

  公开号：US20060094767A1

  公开（公告）日：2006-05-04

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R 1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R 2 represents a group —OR 3 or the like, and R 3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R 1 and —(CH 2 ) n R 2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R 41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis , multi-drug-resistant Mycobacterium tuberculosis , and atypical acid-fast bacteria.

  本发明提供了一种2,3-二氢-6-硝基咪唑并[2,1-b]噁唑化合物，其通式如下：其中，R1代表氢原子或C1-C6烷基，n代表0到6的整数，R2代表—OR3或类似的基团，R3代表氢原子、C1-C6烷基或类似的基团，或者R1和—(CH2)nR2可以通过相邻的碳原子通过氮原子结合在一起形成一个螺环，其通式为（H）：其中，R41为氢、C1-C6烷基或类似的基团。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型酸性快速细菌具有优异的杀菌作用。
• 2,3-DIHYDRO-6-NITROIMIDAZO 2,1-b OXAZOLES
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP1555267A1

  公开（公告）日：2005-07-20

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R2 represents a group -OR3 or the like, and R3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R1 and -(CH2)nR2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and a typical acid-fast bacteria.

  本发明提供了由以下通式代表的 2，3-二氢-6-硝基咪唑并[2，1-b]恶唑化合物： 其中R1代表氢原子或C1-C6烷基，n代表0至6的整数，R2代表基团-OR3或类似基团，R3代表氢原子、C1-C6烷基或类似基团，或者R1和-(CH2)nR2可以通过氮原子与相邻的碳原子相互结合，从而形成通式(H)代表的螺环： 其中 R41 为氢、C1-C6 烷基或类似基团。本化合物对结核分枝杆菌、多重耐药结核分枝杆菌和典型的耐酸细菌有很好的杀菌作用。
• 2,3-dihydro-6-nitroimidazo[2,1-b]oxazoles compound
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP2570418A2

  公开（公告）日：2013-03-20

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R2 represents a group -OR3 or the like, and R3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R1 and -(CH2)nR2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and atypical acid-fast bacteria.

  本发明提供了一种由以下通式表示的 2,3-二氢-6-硝基咪唑并[2,1-b]恶唑化合物： 其中R1代表氢原子或C1-C6烷基，n代表0至6的整数，R2代表基团-OR3或类似基团，R3代表氢原子、C1-C6烷基或类似基团，或者R1和-(CH2)nR2可以通过氮原子与相邻的碳原子相互结合，从而形成通式(H)代表的螺环： 其中 R41 为氢、C1-C6 烷基或类似基团。本化合物对结核分枝杆菌、多重耐药结核分枝杆菌和非典型耐酸菌有很好的杀菌作用。
• DENTALMATERIALIEN AUF BASIS VON CYCLOPOLYMERISIERBAREN VERNETZERN
  申请人：Ivoclar Vivadent AG

  公开号：EP3861976A1

  公开（公告）日：2021-08-11

  Dentalwerkstoff der mindestens eine Verbindung der Formeln I enthält, in der R1 ein linearer, verzweigter oder cyclischer aliphatischer C1-C30-Kohlenwasserstoffrest oder ein aromatischer C6-C30-Kohlenwasserstoffrest ist, wobei der aliphatische oder aromatische Kohlenwasserstoffrest substituiert oder unsubstituiert sein kann und wobei aliphatische Kohlenwasserstoffreste durch eine oder mehrere Urethangruppen, Estergruppen, Sauerstoffatome und/oder Schwefelatome unterbrochen sein können; X, Y, Z unabhängig voneinander jeweils -COOR2-, -CON(R3R4)-, ein aromatischer C6-C10-Kohlenwasserstoffrest oder CN sind, wobei R2, R3, R4 jeweils unabhängig voneinander Wasserstoff, ein linearer, verzweigter oder cyclischer aliphatischer C1-C30-Kohlenwasserstoffrest oder ein aromatischer C6-C30-Kohlenwasserstoffrest ist, wobei der aliphatische oder aromatische Kohlenwasserstoffrest substituiert oder unsubstituiert sein kann und wobei aliphatische Kohlenwasserstoffreste durch ein oder mehrere Sauerstoffatome unterbrochen sein können, und m 2 oder 3 ist.

  含有至少一种式 I 化合物的牙科材料、 其中 R1 是线性、支链或环状脂族 C1-C30 烃基或芳香族 C6-C30 烃基，其中脂族或芳香族烃基可以是取代或未取代的，脂族烃基可以被一个或多个氨基甲酸酯基团、酯基、氧原子和/或硫原子打断；X、Y、Z 各自独立地互为-COOR2-、-CON(R3R4)-、C6-C10 芳烃基或 CN，其中 R2、R3、R4 各自独立地互为氢、线性、支链或环状 C1-C30 脂肪族烃基或 C6-C30 芳烃基、其中脂肪烃基或芳香烃基可以是取代的或未取代的，脂肪烃基可以被一个或多个氧原子打断，m 为 2 或 3。
• 893. Syntheses of heterocyclic compounds. Part IV. Oxidative cyclisation of aromatic amines and their N-acyl derivatives
  作者：O. Meth-Cohn、H. Suschitzky

  DOI：10.1039/jr9630004666

  日期：——