Structural studies on monohalogenated derivatives of the phytohormone indole-3-acetic acid (auxin) was written by Nigovic, Biljana;Kojic-Prodic, Biserka;Antolic, Snjezana;Tomic, Sanja;Puntarec, Vitomir;Cohen, Jerry D.. And the article was included in Acta Crystallographica, Section B: Structural Science in 1996.Synthetic Route of C10H8ClNO2 This article mentions the following:
The physiol. properties of the phytohormone (auxin) indole-3-acetic acid (IAA) and its ring substituted derivatives have so far been rationalized by a number of contradictory hypotheses based on incomplete structural data deduced mainly by inspection of mol. models. To give more evidence for structure-activity relations of monohalogenated IAA’s, the mol. structures of the natural auxin 4-Cl-IAA as well as 5-Cl-IAA, 6-Cl-IAA, 7-Cl-IAA and 5-Br-IAA are compared, as revealed by x-ray anal., and mol. mechanics and dynamics. The influence of the substitution site and the size of the halogen atom and bioactivity is discussed. The typical structural feature of the mols. studied is the slight distortion of part of the indole nucleus around C7: bond length C6-C7 1.368(6) 脜 and C6-C7-C71 117.6(3)掳 (average values of five structures and seven mols.). The conformations of monohalogenated indole-3-acetic acid mols., characteristic for auxins, are defined by rotations about two bonds only: one describes the relative orientation of a side chain towards the indole moiety and the 2nd the orientation of the carboxylic group. The results of x-ray structure anal., and mol. mechanics and dynamics revealed the folded shape of the mols. in all compounds studied. Ab initio calculations showed that the planar conformation can be adopted as well. Crystal data at 297 K for 4-Cl-IAA, 6-Cl-IAA, 7-Cl-IAA and 5-Br-IAA, and at 220 K for 5-Cl-IAA are as follows: 4-Cl-IAA, monoclinic, space group P21/c, a 7.313(4), b 17.156(4), c 7.640(4) 脜, 尾 92.71(5)掳, Z = 4, dc = 1.454, R = 0.037, Rw = 0.039 for 1040 reflections; 5-Cl-IAA, monoclinic, space group P21/c, a 19.141(4), b 5.154(2), c 10.323(3) 脜, 尾 116.23(2)掳, Z = 4, dc = 1.524, R = 0.039, Rw = 0.042 for 1184 reflections; 6-Cl-IAA, orthorhombic, space group Pbca, a 61.08(1), b 12.115(7), c 7.674(5) 脜, Z = 8 (3 mols./Z), dc = 1.471, R = 0.052, Rw = 0.052 for 3030 reflections; 7-Cl-IAA, monoclinic, space group P21/c, a 20.244(5), b 4.829(2), c 10.728(4) 脜, 尾 116.30(1)掳, Z = 4, dc = 1.481, R = 0.042, Rw = 0.029 for 889 reflections; 5-Br-IAA, triclinic, space group P1虆, a 5.645(3), b 9.713(4), c 10.019(4) 脜, 伪 116.02(3), 尾 92.67(5), 纬 100.12(4)掳, Z = 2, dc = 1.754, R = 0.029, Rw = 0.020 for 1865 reflections. At. coordinates are given. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Synthetic Route of C10H8ClNO2).
2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C10H8ClNO2
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles