1-(1,2-二氨基-2-丙基)环丙烷羧酸 | 915867-73-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1-(1,2-二氨基-2-丙基)环丙烷羧酸
• 英文名称: 1-(1,2-diamino-1-methylethyl)-1-cyclopropanecarboxylic acid
• 英文别名: 1-(1,2-Diaminopropan-2-YL)cyclopropanecarboxylic acid；1-(1,2-diaminopropan-2-yl)cyclopropane-1-carboxylic acid
• CAS: 915867-73-1
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: CQOHXYQXWCMUTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.6±12.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  89.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1,2-二氨基-2-丙基)环丙烷羧酸 在 六甲基二硅氮烷 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 9.0h， 生成 tert-butyl (7-methyl-4-oxo-5-azaspiro[2.4]hept-7-yl)carbamate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Novel 7-[7-Amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-8-methoxyquinolines with Potent Antibacterial Activity against Respiratory Pathogens

  摘要：

  Novel 7-[7-amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]- 8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 2a and 2b were designed and synthesized to obtain potent antibacterial drugs for the treatment of respiratory tract infections. Among these, compound 2a possessing (S)-configuration for the asymmetrical carbon on the pyrolidine moiety at the C-7 position of the quinolone scaffold exhibited potent in vitro antibacterial activity against respiratory pathogens including Gram-positive (Streptococcus pneumoniae and Staphylococcus aureus), Gram-negative (Haemophilus influenzae and Moraxcella catarrhalis), and atypical strains (Chalmydia pneumoniae and Mycoplasma pneumoniae), as well as multidrug-resistant Streptococcus pneumoniae and quinolone-resistant and methicillin-resistant Staphylococcus aureus). Furthermore, compound 2a showed excellent in vivo activity against the experimental murine pneumonia model due to multidrug resistant Streptococcus pneumoniae (MDRSP) and favorable profiles in preliminary toxicological and nonclinical pharmacokinetic studies.

  DOI：

  10.1021/jm301650g
• 作为产物：
  描述：

  1-(1-amino-1-cyanoethyl)-1-cyclopropanecarboxylic acid tert-butyl ester 在 盐酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 6.5h， 生成 1-(1,2-二氨基-2-丙基)环丙烷羧酸
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Novel 7-[7-Amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-8-methoxyquinolines with Potent Antibacterial Activity against Respiratory Pathogens

  摘要：

  Novel 7-[7-amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]- 8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 2a and 2b were designed and synthesized to obtain potent antibacterial drugs for the treatment of respiratory tract infections. Among these, compound 2a possessing (S)-configuration for the asymmetrical carbon on the pyrolidine moiety at the C-7 position of the quinolone scaffold exhibited potent in vitro antibacterial activity against respiratory pathogens including Gram-positive (Streptococcus pneumoniae and Staphylococcus aureus), Gram-negative (Haemophilus influenzae and Moraxcella catarrhalis), and atypical strains (Chalmydia pneumoniae and Mycoplasma pneumoniae), as well as multidrug-resistant Streptococcus pneumoniae and quinolone-resistant and methicillin-resistant Staphylococcus aureus). Furthermore, compound 2a showed excellent in vivo activity against the experimental murine pneumonia model due to multidrug resistant Streptococcus pneumoniae (MDRSP) and favorable profiles in preliminary toxicological and nonclinical pharmacokinetic studies.

  DOI：

  10.1021/jm301650g

文献信息

• Tri-, tetra-substituted-3-aminopyrrolidine derivative
  申请人：Takahashi Hisashi

  公开号：US20060264428A1

  公开（公告）日：2006-11-23

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by following formula (I): wherein R 1 and R 2 represent hydrogen atom, or the like; R 3 represents an alkyl group containing 1 to 6 carbon atoms, or the like; R 4 and R 5 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like, with the proviso that R 4 and R 5 do not simultaneously represent hydrogen atom; or the substituents R 4 and R 5 together represent (a) a 3- to 6-membered cyclic structure including the carbon atom shared by R 4 and R 5 to form a spirocyclic structure with the pyrrolidine ring; R 6 and R 7 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like; R 8 represents a halogen-substituted alkyl group containing 1 to 6 carbon atoms, or the like; X 1 represents hydrogen atom or a halogen atom; A represents nitrogen atom or a moiety represented by formula (II):

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，对革兰氏阳性和革兰氏阴性细菌均表现出广谱和强效的抗菌活性，并且具有很高的安全性。所提供的化合物由以下式（I）表示： 其中R1和R2代表氢原子，或类似物；R3代表含有1至6个碳原子的烷基基团，或类似物；R4和R5独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物，但R4和R5不同时代表氢原子；或取代基R4和R5一起代表（a）包括由R4和R5共享的碳原子形成螺环结构与吡咯烷环形成螺环结构的3至6成员环结构；R6和R7独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物；R8代表含有1至6个碳原子的卤代烷基基团，或类似物；X1代表氢原子或卤原子；A代表氮原子或由式（II）表示的基团。
• TRI-, TETRA-SUBSTITUTED-3-AMINOPYRROLIDINE DERIVATIVE
  申请人：TAKAHASHI Hisashi

  公开号：US20090253726A1

  公开（公告）日：2009-10-08

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by formula (I):

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，具有广谱和强大的抗菌活性，对革兰氏阳性和革兰氏阴性细菌均有作用，并且非常安全。所提供的化合物由式（I）表示。
• METHOD FOR PRODUCING ASYMMETRIC TETRASUBSTITUTED CARBON ATOM-CONTAINING COMPOUND
  申请人：Tani Yuichiro

  公开号：US20090054648A1

  公开（公告）日：2009-02-26

  The invention provides an industrial method for producing a spiroaminopyrrolidone derivative, which is an intermediate for producing a quinolone antibacterial agent. The invention provides a method for producing a compound represented by formula (2): (wherein n is an integer of 2 to 5; R 1 represents a (substituted) alkyl group or a (substituted) aryl group; and R 2 represents a (substituted) alkoxycarbonyl group, a (substituted) aralkyloxycarbonyl group, a (substituted) aliphatic acyl group, or a (substituted) aromatic acyl group), which includes treating a compound represented by formula (1): (wherein n, R 1 , and R 2 are the same as defined above; and R 3 represents a hydrogen atom, a (substituted) alkyl group, or a (substituted) aralkyl group) under a hydrogen gas atmosphere in the presence of a metallic catalyst.

  本发明提供了一种工业方法，用于生产螺环氨基吡咯烷衍生物，该衍生物是生产喹诺酮类抗菌剂的中间体。本发明提供了一种生产由式（2）表示的化合物的方法：（其中n是2至5的整数；R1表示（取代）烷基或（取代）芳基；R2表示（取代）烷氧羰基，（取代）芳基烷氧羰基，（取代）脂肪酰基或（取代）芳香酰基），其包括在金属催化剂存在下，在氢气气氛下处理由式（1）表示的化合物：（其中n，R1和R2如上定义；R3表示氢原子，（取代）烷基或（取代）芳基烷基）。
• TRI- OR TETRA-SUBSTITUTED-3-AMINOPYRROLIDINE DERIVATIVES
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1882689A1

  公开（公告）日：2008-01-30

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by following formula (I): wherein R1 and R2 represent hydrogen atom, or the like; R3 represents an alkyl group containing 1 to 6 carbon atoms, or the like; R4 and R5 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like, with the proviso that R4 and R5 do not simultaneously represent hydrogen atom; or the substituents R4 and R5 together represent (a) a 3- to 6-membered cyclic structure including the carbon atom shared by R4 and R5 to form a spirocyclic structure with the pyrrolidine ring; R6 and R7 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like; R8 represents a halogen-substituted alkyl group containing 1 to 6 carbon atoms, or the like; X1 represents hydrogen atom or a halogen atom; A represents nitrogen atom or a moiety represented by formula (II):

  本发明提供了一种喹诺酮类合成抗菌剂和一种治疗感染的药物，对革兰氏阳性菌和革兰氏阴性菌均具有广谱、强效的抗菌活性，而且安全性高。所提供的化合物由下式(I)表示： 其中 R1 和 R2 代表氢原子或类似物；R3 代表含有 1 至 6 个碳原子的烷基或类似物；R4 和 R5 独立地代表氢原子、含有 1 至 6 个碳原子的烷基或类似物，但 R4 和 R5 不同时代表氢原子；或取代基 R4 和 R5 共同代表 (a) 3 至 6 元环状结构，包括 R4 和 R5 共用的碳原子，与吡咯烷环形成螺环结构；R6 和 R7 独立代表氢原子、含 1 至 6 个碳原子的烷基或类似物；R8 代表含 1 至 6 个碳原子的卤素取代烷基或类似物；X1 代表氢原子或卤素原子；A 代表氮原子或式 (II) 所代表的分子：
• Tri-or tetra-substituted-3-aminopyrrolidine deritatives
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2463274A1

  公开（公告）日：2012-06-13

  A compound of the following formula (19) or (20): wherein R11 represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, a cycloalkyl group containing 3 to 6 carbon atoms, or a substituted carbonyl group derived from an amino acid, a dipeptide, or a tripeptide, or a protective group of the amino acid; the alkyl group being optionally substituted with a substituent selected from the group consisting of hydroxy group, amino group, halogen atom, an alkylthio group containing 1 to 6 carbon atoms, and an alkoxy group containing 1 to 6 carbon atoms; R21 represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or a cycloalkyl group containing 3 to 6 carbon atoms or a protective group of the amino acid; the alkyl group being optionally substituted with a substituent selected from the group consisting of hydroxy group, amino group, halogen atom, an alkylthio group containing 1 to 6 carbon atoms, and an alkoxy group containing 1 to 6 carbon atoms; R3 represents a methyl group; ethyl group; vinyl group; fluoro-substituted methyl group or ethyl group; methyl group or ethyl group having amino group or hydroxy group; and methyl group having thiomethyl group or methoxy group; R4 and R5 together form cyclopropane ring or cyclobutane ring including the carbon atom shared by R4 and R5 to form a spirocyclic structure; R6 and R7 independently represent hydrogen atoms, and R13 represents protective group of the amino group.

  下式(19)或(20)的化合物： 其中 R11 代表氢原子、含 1 至 6 个碳原子的烷基、含 3 至 6 个碳原子的环烷基、或衍生自氨基酸、二肽或三肽的取代羰基、或氨基酸的保护基；烷基可任选被选自羟基、氨基、卤素原子、含 1 至 6 个碳原子的烷硫基和含 1 至 6 个碳原子的烷氧基的取代基所取代； R21 代表氢原子、含 1 至 6 个碳原子的烷基、含 3 至 6 个碳原子的环烷基或氨基酸的保护基；该烷基可任选被选自羟基、氨基、卤素原子、含 1 至 6 个碳原子的烷硫基和含 1 至 6 个碳原子的烷氧基组成的取代基取代； R3 代表甲基；乙基；乙烯基；氟取代的甲基或乙基；具有氨基或羟基的甲基或乙基； 以及具有硫代甲基或甲氧基的甲基； R4 和 R5 共同形成环丙烷环或环丁烷环，包括 R4 和 R5 共有的碳原子，形成螺环结构； R6 和 R7 分别代表氢原子，以及 R13 代表氨基的保护基团。